3.1 Piperidine hydrochloride

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PubChem

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Reactions (112)

Yield

Substances (3)

Conditions

Citations (85)

References A

B

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1

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A: 91%

24 h; Darkness;

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Kyran, Samuel J.; Sanchez, Sergio G.; Arp, Christopher J.; Darensbourg, Donald J.

Organometallics, 2015 , vol. 34, # 14 p. 3598 - 3602 Title/Abstract

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A

2

B

C

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Rx-ID: 41255146 Find similar reactions

A: 4% B: 95% C: 1%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

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B

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3

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A: 79% B: 15%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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1:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

A

4

B

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Rx-ID: 41255159 Find similar reactions

A: 75% B: 12%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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11:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

5

A

B

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Rx-ID: 41255162 Find similar reactions

A: 71% B: 20%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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13:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

6

B

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Synthesize Find similar Rx-ID: 41255164 Find similar reactions

A

A: 68% B: 12%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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14:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

7

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B

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Rx-ID: 41255165 Find similar reactions

A: 82% B: 11%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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2:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

8

A

B

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Synthesize Find similar Rx-ID: 41255166 Find similar reactions

A: 76% B: 18%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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16:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

A

9

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C

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Rx-ID: 41255168 Find similar reactions

A: 76% B: 14% C: 6%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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17:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

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10

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Rx-ID: 41255170 Find similar reactions

A: 80% B: 15%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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1:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

A

B

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11

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A: 68% B: 14%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

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Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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4:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluent-

hexane/EtOAc).

A

B

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12

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Rx-ID: 41255197 Find similar reactions

A: 63% B: 22%

in 1,4-dioxane

2 h; Reflux; Hide Experimental Procedure

Mamedov, Vakhid A.; Hafizova, Elena A.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh.; Mirgorodskaya, Alla B.; Zakharova, Lucia Ya.; Latypov, Shamil K.; Sinyashin, Oleg G.

Tetrahedron, 2015 , vol. 71, # 48 p. 9143 - 9153 Title/Abstract

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15:General procedure for the synthesis of 5

General procedure: A mixture of alkyl 3-chloro(or bromo)-2-oxo-3-arylpropanoate 2 (3.0 mmol), 1-cyclohexenylpiperidine (or 4-tert-butyl-1-cyclohexenylpiperidine) 4a(b) (5.2 mmol) and dioxane (30 mL) was heated at reflux for 2 h. After cooling down to room temperature, the precipitate was filtered and recrystallized in toluene (or washed with i-PrOH) to give piperidinium chloride (or bromide) 6. The solvent was removed to give a slightly brown crude product 5, which was purified on column chromatography with silica gel (eluenthexane/EtOAc).

13

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80%

Stage #1: With C46H178O41Si42; titanium (IV) isopropoxide in toluene

T=100°C; 24 h; Inert atmosphere; Stage #2: With hydrogenchloride; water in toluene

T=20°C; 4 h; Inert atmosphere; chemoselective reaction; Hide Experimental Procedure

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Rx-ID: 37108156 Find similar reactions

Laval, Stephane; Dayoub, Wissam; Pehlivan, Leyla; Metay, Estelle; Favre-Reguillon, Alain; Delbrayelle, Dominique; Mignani, Gerard; Lemaire, Marc

Tetrahedron, 2014 , vol. 70, # 4 p. 975 - 983 Title/Abstract

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3:4.4. General procedure for the reduction of dinitriles

General procedure: To a 50 mL round-bottom flask, under nitrogen atmosphere, containing dinitriles 1p (500 mg, 4.2 mmol, 1.0 equiv) in 5.0 mL of toluene were added PMHS (1.0 mL, 16.8 mmol, 4.0 equiv) and Ti(Oi-Pr)4 (1.3 mL, 4.3 mmol, 1.0 equiv). The mixture was then heated at 100°C for 24 h (the colorless solution turned into deep purple). After cooling to rt, the clear solution was diluted in toluene (30 mL) and hydrolyzed with aqueous 1M HCl (15 mL, 3.6 equiv) for 4 h (until the deep purple solution became yellow). The crude mixture was then concentrated under reduced pressure. The resulting solid was filtered, washed with pentane (60 mL), dissolved in chloroform and filtrate on a pad of Celite®. The filtrate was finally concentrated under reduced pressure affording the amine 3p as a hydrochloride salt.

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14

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Rx-ID: 38051285 Find similar reactions

With dichloromethane

T=20°C; 24 h;

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Kociecka, Paulina; Kochel, Andrzej; Szymanska-Buzar, Teresa

Inorganic Chemistry Communications, 2014 , vol. 45, p. 105 - 107 Title/Abstract

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B

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15

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Rx-ID: 34809307 Find similar reactions

A: 60%

in toluene

T=111°C; 48 h; Inert atmosphereSchlenk techniqueReflux;

Maiti, Swarup K.; Jardim, Manuel G.; Rodrigues, Joao; Rissanen, Kari; Campo, Jochen; Wenseleers, Wim

Organometallics, 2013 , vol. 32, # 2 p. 406 - 414 Title/Abstract

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A

B

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16

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A: 62% B: 37%

With 4-methylphenyl chlorosulfate; 2,6diisopropylphenyl chlorosulfate

T=-78°C; 18 h; Inert atmosphereSealed tube;

Debergh, J. Robb; Niljianskul, Nootaree; Buchwald, Stephen L.

Journal of the American Chemical Society, 2013 , vol. 135, # 29 p. 10638 - 10641 Title/Abstract

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A

B

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17

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A: 90 %Spectr.

B: 10 %Spectr.

With 5 Rh on charcoal; hydrogen in water

T=50°C; P=150 Torr; 16 h; Hide Experimental Procedure

Fussell, Steven J.; Luan, Amy; Peach, Philip; Scotney, Gemma

Tetrahedron Letters, 2012 , vol. 53, # 8 p. 948 - 951 Title/Abstract

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Preparation of 4-(4-iodo-pyrazol-1-yl)piperidine (2)

A solution of 4-(1H-pyrazol-1-yl)pyridine hydrochloride 10 (20.0 g, 110.1 mmol) in deionised water (200 mL) was hydrogenated over catalyst (5percent Rh/C 20A, 2.0 g) with overhead stirring, at 150psi for 16 hours at 50°C. The catalyst was removed by filtration to give a solution of 4-(1H-pyrazol-1-yl)piperidine hydrochloride 11 (90percent in-situ yield, 200 mL). To this solution was added 37wtpercent concentrated HCl aqueous solution (9.46 ml, 110.1 mmol) followed by N-iodosuccinimide (24.77 g, 110.1 mmol) at 20°C under nitrogen. After stirring for 30mins, the reaction mixture was quenched with sodium sulfite (6.0 g, 47.6 mmol). THF (200 mL) was added and aqueous phase was pH adjusted to 12 by adding 50wtpercent NaOH aqueous solution (20 mL) at 10-20°C. The biphasic mixture was stirred at 20°C for 30mins and the aqueous phase washed with THF (60 mL). The combined THF phases were strip and replaced into ethyl acetate (60 mL) at reduced pressure, the product was isolated at 20°C by filtration, washed with further ethyl acetate (20 mL) and dried at 50°C under vacuum.

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18

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Multi-step reaction with 2 steps 1.1: acetonitrile / 24 h / Inert atmosphere; Reflux; Large scale reaction 1.2: 0.5 h / 20 - 25 °C / Inert atmosphere; Large scale reaction 2.1: 5 Rh on charcoal; hydrogen / water / 16 h / 50 °C / 150 Torr View Scheme

Fussell, Steven J.; Luan, Amy; Peach, Philip; Scotney, Gemma

Tetrahedron Letters, 2012 , vol. 53, # 8 p. 948 - 951 Title/Abstract

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A

19

B

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Rx-ID: 29856167 Find similar reactions

With oxygen; gold

T=60°C; P=760.051 Torr; 24 h;

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A

B

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Zhou, Yibo; Angelici, Robert J.; Keith Woo

Catalysis Letters, 2010 , vol. 137, # 1-2 p. 8 - 15 Title/Abstract

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20

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Rx-ID: 29955918 Find similar reactions

A: 80%

in diethyl ether

T=15°C; Reflux;

Potkin; Petkevich; Kurman

Russian Journal of Organic Chemistry, 2010 , vol. 46, # 9 p. 1305 - 1312 Title/Abstract

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A

B

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21

Synthesize Find similar Rx-ID: 29955919 Find similar reactions

A: 79%

in diethyl ether

T=15°C; Reflux;

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Potkin; Petkevich; Kurman

Russian Journal of Organic Chemistry, 2010 , vol. 46, # 9 p. 1305 - 1312 Title/Abstract

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22

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Rx-ID: 5008490 Find similar reactions

98%

With trichloroethane, 1,1,2-; 10 palladium on activated carbon; hydrogen in methanol

P=760.051 Torr; 1 h; chemoselective reaction;

Cheng, Chuanjie; Sun, Jianwei; Xing, Lixin; Xu, Jimin; Wang, Xinyan; Hu, Yuefei

Journal of Organic Chemistry, 2009 , vol. 74, # 15 p. 5671 - 5674 Title/Abstract

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97%

With dichloromethane; hydrogen; palladium on activated charcoal in methanol

T=20°C; 24 h; atmospheric pressure;

Wang, Xinyan; Dong, Yanmei; Sun, Jianwei; Xu, Xuenong; Li, Rui; Hu, Yuefei

Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1897 - 1900 Title/Abstract

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82%

With Na2K-SG(I) in tetrahydrofuran

T=20°C; Inert atmosphere;

Nandi, Partha; Dye, James L.; Jackson, James E.

Tetrahedron Letters, 2009 , vol. 50, # 27 p. 3864 - 3866 Title/Abstract

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With hydrogenchloride; chloroformic acid vinyl ester

1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.) MeOH, 50-60 deg C, 4.5 h; Yield given. Multistep reaction;

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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23

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88%

With Na2K-SG(I) in tetrahydrofuran

T=20°C; Inert atmosphere;

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Rx-ID: 28649852 Find similar reactions

Nandi, Partha; Dye, James L.; Jackson, James E.

Tetrahedron Letters, 2009 , vol. 50, # 27 p. 3864 - 3866 Title/Abstract

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A

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24

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Rx-ID: 28950949 Find similar reactions

in water; acetone

T=25°C; Kinetics; Concentration;

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Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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A

B

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25

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Rx-ID: 28950950 Find similar reactions

in water; acetonitrile

T=25°C; Kinetics; Concentration;

Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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A

B

C

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26

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With water in acetone

T=25°C; Kinetics; ConcentrationTimeSolvent;

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Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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A

B

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27

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Rx-ID: 28950952 Find similar reactions

in water; acetone

T=25°C; Kinetics; ConcentrationSolvent;

Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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A

B

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28

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Rx-ID: 28950953 Find similar reactions

in water; acetone

T=25°C; Kinetics; Concentration;

Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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A

B

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29

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in water; acetone

T=25°C; Kinetics; ConcentrationSolvent;

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Streidl, Nicolas; Antipova, Anna; Mayr, Herbert

Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7328 - 7334 Title/Abstract

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30

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99%

Hide Experimental Procedure

Rx-ID: 23861514 Find similar reactions

Barta, Thomas E.; Arner, Elizabeth C.; Becker, Daniel; Boehm, Terri L.; DeCrescenzo, Gary A.; McDonald, Joseph

Patent: US2003/171404 A1, 2003 ; Title/Abstract

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22.B:Preparation of N-hydroxy-2,3-dimethoxy-6-[[4-[(2'-biphenyl]-4-yl)-oxy-1-piperidinyl]sulfonyl]benzamide

Part B: To a solution of the bromide of part A (20 mmol, 7.2 g) in L) was added 4N HCl (50 mL).

The solution was stirred at ambient or 2 hr and then concentrated to give a solid.

The solid was triturated ther, affording the desired piperidine hydrochloride (5.8 g 99percent).

99%

Hide Experimental Procedure

Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; DeCrescenzo, Gary A.; Freskos, John N.; Getman, Daniel P.; McDonald, Joseph J.; Mischke, Brent V.; Rao, Shashidhar N.; Villamil, Clara I.

Patent: US2003/73845 A1, 2003 ; Title/Abstract

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Pharmacia Corporation

Patent: US6696449 B2, 2004 ; Title/Abstract

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22.B:Preparation of N-hydroxy-2,3-dimethoxy-6-[[4-[(2'-methoxy[1,1'-biphenyl]-4-yl)-oxy-1-piperidinyl]sulfonyl]benzamide

Part B: To a solution of the bromide of part A (20 mmol, 7.2 g) in dioxane (20 mL) was added 4N HCl (50 mL).

The solution was stirred at ambient temperature for 2 hr and then concentrated to give a solid.

The solid was triturated with diethyl ether, affording the desired piperidine hydrochloride (5.8 g 99percent).

88%

Hide Experimental Procedure

Barta, Thomas E.; Arner, Elizabeth C.; Becker, Daniel; Boehm, Terri L.; DeCrescenzo, Gary A.; McDonald, Joseph

Patent: US2003/171404 A1, 2003 ; Title/Abstract

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21.B:Preparation of N-hydroxy-2-[[4-(4-pyridinyloxy)-1-piperidinyl]sulfonyl]benzamide, Monohydrochloride

Part B: A solution of HCl in 1,4-dioxane (20 mL of a 4 N solution, 80 mmol) is added to a solution of pyridyloxypiperidine of Part A (3.81 g, 13.7 mmol) in 1,4-dioxane (28 mL) at ambient temperature.

After 1 hr, the suspension is concentrated and the residue triturated with hot isopropanol.

The resulting solid is dried at 50° C. under vacuum to afford the desired piperidine hydrochloride salt as a white powder (3.03 g, 88percent).

Analytical calculation for C10H14N2O.2HCl: C, 47.82; H, 6.42; N, 11.15. Found: C, 47.40; H, 6.64; N, 11.04.

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88%

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G. D. Searle and Co.,

Patent: US2003/191317 A1, 2003 ; Title/Abstract

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21.B:Preparation of N-Hydroxy-2-[[4-(4-pyridinyloxy)-1-piperidinyl]sulfonyl]-benzamide, monohydrochloride

Part B: A solution of hydrogen chloride in 1,4-dioxane (20 mL of a 4 N solution, 80 mmol) is added to a solution of pyridyloxypiperidine of Part A (3.81 g, 13.7 mmol) in 1,4-dioxane (28 mL) at ambient temperature.

After one hour, the suspension is concentrated and the residue triturated with hot iso-propanol.

The resulting solid is dried at 50 degrees Celsius under vacuum to afford the desired piperidine hydrochloride salt as a white powder (3.03 g, 88percent).

Analytical calculation for C10H14N20.2HCl: C, 47.82; H, 6.42; N, 11.15. Found: C, 47.40; H, 6.64; N, 11.04.

88%

Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; DeCrescenzo, Gary A.; Freskos, John N.; Getman, Daniel P.; McDonald, Joseph J.; Mischke, Brent V.; Rao, Shashidhar N.; Villamil,

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Clara I.

Patent: US2003/73845 A1, 2003 ; Title/Abstract

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21.B:Preparation of N-hydroxy-2-[[4-(4-pyridinyloxy)-1-piperidinyl]sulfonyl]benzamide, monohydrochloride

Part B: A solution of HCl in 1,4-dioxane (20 mL of a 4 N solution, 80 mmol) is added to a solution of pyridyloxypiperidine of Part A (3.81 g, 13.7 mmol) in 1,4-dioxane (28 mL) at ambient temperature.

After 1 hr, the suspension is concentrated and the residue triturated with hot isopropanol.

The resulting solid is dried at 50° C. under vacuum to afford the desired piperidine hydrochloride salt as a white powder (3.03 g, 88percent).

Analytical calculation for C10H14N2O, HCl: C, 47.82; H, 6.42; N, 11.15. Found: C, 47.40; H, 6.64; N, 11.04.

88%

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Pharmacia Corporation

Patent: US6696449 B2, 2004 ; Title/Abstract

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21.B:Preparation of N-hydroxy-2-[[4-(4-pyridinyloxy)-1-piperidinyl]sulfonyl]benzamide, monohydrochloride

Part B: A solution of HCl in 1,4-dioxane (20 mL of a 4 N solution, 80 mmol) is added to a solution of pyridyloxypiperidine of Part A (3.81 g, 13.7 mmol) in 1,4-dioxane (28 mL) at ambient temperature.

After 1 hr, the suspension is concentrated and the residue triturated with hot isopropanol.

The resulting solid is dried at 50° C. under vacuum to afford the desired piperidine hydrochloride salt as a white powder (3.03 g, 88percent).

Analytical calculation for C10H14N2O, HCl: C, 47.82; H, 6.42; N, 11.15. Found: C, 47.40; H, 6.64; N, 11.04.

10%

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Warner-Lambert Company

Patent: US5977141 A1, 1999 ; Title/Abstract

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EXAMPLES

The 1,2,5,6-tetrahydropyridine (3) is reduced by catalytic reduction using a suitable catalyst such as 10percent palladium on carbon (Pd/C) and hydrogen gas (H2) at pressures between 10 p.s.i. and 100 p.s.i. in a suitable solvent such as absolute ethanol, acetic acid, or tetrahydrofuran to yield the piperidine hydrochloride (4).

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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(+-)-Solenopsin A*HCl. trans-2-methyl-6-n-undecylpiperidine hydrochloride

(+-)-Solenopsin A*HCl. trans-2-methyl-6-n-undecylpiperidine hydrochloride To a stirred solution of 0.463 g of trans-N-Boc-2-methyl-6-n-undecylpiperidine in 50 ml of CH2Cl2 at 0° C. was added dropwise 12.2 mL (excess) of trifluoroacetic acid.

The cooling bath was removed, and stirring was continued for 1 h at room temperature.

After concentrating the resulting solution on a rotary evaporator, the remaining liquid was dissolved in ether (50 mL), and 25 ml of water was added.

The aqueous phase was extracted with ether (2*40 mL), and the combined organic extracts were washed with saturated NaHCO3 (2*40 mL) and brine.

The organic phase was dried over K2CO3, filtered through Celite, and concentrated in vacuo to give an oil.

The crude product was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as white needles. 1H NMR (300 MHz) δ9.30 (br s, 2 H), 3.53 (br s, 1 H), 3.27 (br s, 1 H), 1.96-1.22 (m, 29 H), 0.85 (t, 3 H); 13C NMR (75 MHz) 52.0 (s), 48.2 (s), 32.1 (s), 31.0 (s), 29.8 (s), 29.75 (s), 29.7 (s), 29.6 (s), 2.95 (s), 29.2 (s), 26.5 (s), 26.1 (s), 22.9 (s), 17.6 (s), 17.1 (s), 14.3 (s) ppm. FT-IR (neat) 3420, 2931, 2853, 1465, 1376, 1141, 1067 cm-1.

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G. D. Searle and Company

Patent: US6372758 B1, 2002 ; Title/Abstract

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3.2:Preparation of tetrahydro-N-hydroxy-4-[[4-[[4-[(trifluoromethyl)thio]phenyl]-thio]-1-piperidinyl]sulfonyl]-2H-pyran-4-carboxamide

Part 2: Preparation of: To a solution of the product (6 g) of Part 1 in 1,4-dioxane (10 mL) was added 4 N HCl in dioxane (50 mL, 200 mmol).

The mixture stirred at room temperature until starting material was gone by LC (about one hr).

The solvents were then removed and the residue was slurried in diethyl ether and filtered.

The solid was washed with diethyl ether (2*-50 mL) and dried in vacuo to afford the piperidine HCl salt as a white solid (6 g).

1H NMR and mass spectrum showed the desired compound as the HCl salt.

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Eli Lilly and Company

Patent: US6444688 B1, 2002 ; Title/Abstract

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4:Preparation of compound 7:

EXAMPLE 4 Preparation of compound 7: Reaction of compound 27 (0.42 g, 0.91 mmol), piperidine-hydrochloride (0.56mg, 4.58 mmol), and Al(CH3)3 (2.29 ml, 4.58 mmol) yielded 0.42 g (90percent) of compound 7 as a tan foam.

1H-NMR (CDCl ) δ 7.79 (d, J=9.0 Hz, 2H), 7.52 (d, J=8.8 Hz, 1H), 7.30-7.35 (m, 3H), 6.96 (dd, J=9.0 Hz, 2.9 Hz, 1H), 6.82 (d, J=8.7 Hz, 2H), 6.78 (d, J=8.9 Hz, 2H), 4.66 (s, 2H), 3.90 (s, 3H), 3.75 (s, 3H), 3.53 (t, J=4.2 Hz, 2H), 3.42 (t, J=4.2 Hz, 2H), 1.49-1.69 (series of 3

m, 6H); IR (CHCl3) 1639 cm-1; FD+-MS 515 (M+).

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Merck and Co., Inc.

Patent: US5877182 A1, 1999 ; Title/Abstract

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2:Step B

STR73 To a solution of 1.20 g (5.8mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (prepared as described in H. Ong et al J. Med. Chem. 1983, 23, 981-986) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2*10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

The filtrate was concentrated and a small volume of methanol was added followed by ether.

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Merck and Co., Inc.

Patent: US5880125 A1, 1999 ; Title/Abstract

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3:EXAMPLE 3 STR43 Step A: STR44

EXAMPLE 3 STR43 Step A: STR44 To a solution of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (Prepared as described in H. Ong et al., J. Med. Chem., 1983, 23, 981-986) in CH2 Cl2 at 0° C. was added triethylamine and CBZ-Cl and stirred for 1 h at RT. The reaction mixture was poured into 5percent HCl and the aqueous layer was separated.

The aqueous layer was basified with 50percent NaOH to pH=10 and extracted with CH2 Cl2.

The combined organics were washed with brine, dried over K2 C3, and concentrated to yield the desired compound as a thick oil.

To a solution of above product in dry 1,2-dichloroethane at 0° C. was added 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded the piperidine HCl salt as a white solid.

This material was used without purification.

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Merck and Co., Inc.

Patent: US5965565 A1, 1999 ; Title/Abstract

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10:EXAMPLE 10 STR99 Step A: STR100

EXAMPLE 10 STR99 Step A: STR100 To a solution of 1.20 g (5.8 mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (prepared as described in H. Ong et al J. Med. Chem. 1983,23, 981-986) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2*10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

The filtrate was concentrated and a small volume of methanol was added followed by ether.

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Merck and Co., Inc.

Patent: US6123964 A1, 2000 ; Title/Abstract

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1.A:Step A

Step A 1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperdine]hydrochloride To a solution of 1.20 g (5.8 mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (prepared as described by H. Ong, et al., J. Med. Chem., 23, 981-986 (1983)) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2*10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

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Richter Gedeon Vegyeszeti Gyar RT.

Patent: US5198446 A1, 1993 ; Title/Abstract

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2:Preparation of N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}piperidine hydrochloride

EXAMPLE 2 Preparation of N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}piperidine hydrochloride After adding 32.7 g of piperidine to a solution containing 32.5 g of chloromethyl-dimethyl-(4-fluorobenzyl)-silane in 40 ml of xylene, the reaction mixture is refluxed for 6 hours under stirring, then the precipitated piperidine hydrochloride is filtered at 20° C. and washed in 3 portions with a total of 60 ml of benzene.

The filtration is combined with the benzene washings and washed in 3 portions with a total of 150 ml of water and the organic phase is dried over anhydrous magnesium sulfate.

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Merck and Co., Inc.

Patent: US5536716 A1, 1996 ; Title/Abstract

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18.A:Step A

Step A 1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperdine]hydrochloride To a solution of 1.20 g (5.8mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine](prepared as described in H. Ong et al J. Med. Chem. 1983, 23, 981-986) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2*10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

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Eli Lilly and Company

Patent: US5567828 A1, 1996 ; Title/Abstract

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4:Preparation of compound 7:

STR14 Reaction of compound 27 (0.42 g, 0.91 mmol), piperidinehydrochloride (0.56mg, 4.58 mmol), and Al(CH3)3 (2.29 ml, 4.58 mmol) yielded 0.42 g (90percent) of compound 7 as a tan foam.

1 H-NMR (CDCl ) δ7.79 (d, J=9.0 Hz, 2H), 7.52 (d, J=8.8 Hz, 1H), 7.30-7.35 (m, 3H), 6.96 (dd, J=9.0 Hz, 2.9 Hz, 1H), 6.82 (d, J=8.7 Hz, 2H), 6.78 (d, J=8.9 Hz, 2H), 4.66 (s, 2H), 3.90 (s, 3H), 3.75 (s, 3H), 3.53 (t, J=4.2 Hz, 2H), 3.42 (t, J=4.2 Hz, 2H), 1.49-1.69 (series of 3 m, 6H); IR (CHCl3) 1639 cm-1; FD+ -MS 515 (M+).

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Merck and Co., Inc.

Patent: US5559128 A1, 1996 ; Title/Abstract

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5:Step F:.

To a solution of 20 mg of Intermediate 1, 0.020 mL of N-methylmorpholine, 20 mg of EDC and 20 mg of HOBT in 2 mL of CH2 Cl2 was added 11 mg of 3-(5-ethyl-1,2,4-oxadiazolyl)piperidine hydrochloride and stirred for a day at room temperature (the piperidine hydrochloride was prepared in 3 steps from N-t-BOC protected 3-cyanopiperidine by a) addition of hydroxylamine to the nitrile in refluxing methanol, b) acylation of the amino-oxime with propionylchloride in pyridine, and c) deprotection of the N-t-BOC protecting group with HCl (gas) in ethyl acetate).

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Merck and Co., Inc.

Patent: US5767124 A1, 1998 ; Title/Abstract

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1.A:1,2-Dihydro-1-methanesulfonylspiro3H-indole-3,4'-piperdinel hydrochloride

Step A 1,2-Dihydro-1-methanesulfonylspiro3H-indole-3,4'-piperdinel hydrochloride To a solution of 1.20 g (5.8mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (prepared as described by H. Ong, et al., J. Med. Chem., 23, 981-986 (1983)) in 20 niL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mnL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2X10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

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Merck Sharp and Dohme Ltd.

Patent: US5760018 A1, 1998 ; Title/Abstract

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13:4-Phenyl-4-[(1-(3,5-bis(trifluoromethyl)phenyl)-2-aminoethoxy)methyl]

Piperidine Hydrochloride.

Ammonia gas was passed through a solution of the product of Example 9(c) (1.0 g), in dry methanol (50 ml), cooled at -15° C., until saturated.

The reaction flask was sealed with a rubber septum, and allowed to stand at room temperature for 48 hours then the solvents were evaporated at reduced pressure.

The residue was treated with borane-tetrahydrofuran complex (20 ml of a 1.0M solution in tetrahydrofuran), and heated at reflux for 24 hours.

After cooling to room temperature, methanol was added dropwise with caution to destroy excess reagent.

The solvents were evaporated at reduced pressure, the residue dissolved in methanol (20 ml), and the solution allowed to stand at room temperature for 24 hours.

The residue obtained by evaporation of the methanol at reduced pressure, was purified by chromatography on silica gel (eluant 5percent methanol/dichloromethane), to afford the tbutoxycarbonyl-protected piperidine (0.39 g).

This was dissolved in saturated ethereal hydrogen chloride (10 ml) and methanol (1 ml) then allowed to stand at room temperature for 48 hours.

The title compoundcompound was collected as a colourless solid by filtration.

Analysis Calcd. for C22 H24 F6 N2 O. 2 (HCl): C, 50.88; H, 5.05; N, 5.39; Found: C, 50.82; H, 4.98; N, 5.26percent. MS (Cl+) 447 (M+H)+.

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Merck and Co., Inc.

Patent: US5804578 A1, 1998 ; Title/Abstract

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27:EXAMPLE 27 STR99

EXAMPLE 27 STR99 To a solution of 1.20 g (5.8 mmol) of 1'-methyl-1,2-dihydro-spiro[3H-indole-3,4'-piperdine] (prepared as described in H. Ong et al J. Med. Chem. 1983, 23, 981-986) in 20 mL of dry dichloromethane at 0° C. was added triethylamine (0.90 mL; 6.4 mmol) and methanesulfonyl chloride (0.49 mL; 6.35 mmol) and stirred for 30 min.

The reaction mixture was poured into 15 mL of saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2*10 mL).

The combined organics were washed with brine (20 mL), dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure to yield 1.44 g of the methanesulfonamide derivative as pale yellow oil which was used without purification.

To a solution of above crude product in 20 mL of dry 1,2-dichloroethane at 0° C. was added 1.0 mL (9.30 mmol) of 1-chloroethyl chloroformate, and then stirred at RT for 30 min and finally at reflux for 1 h.

The reaction mixture was concentrated to approximately one third of the volume and then diluted with 20 mL of dry methanol and refluxed for 1.5 h.

The reaction was cooled to RT and concentrated to approximately one half of the volume.

The precipitate was filtered and washed with a small volume of cold methanol.

This yielded 1.0 g of the piperidine HCl salt as a white solid.

The filtrate was concentrated and a small volume of methanol was added followed by ether.

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Hoechst Aktiengesellschaft

Patent: US4636513 A1, 1987 ; Title/Abstract

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a:(1)

(a) A solution of 0.4 mol (34.1 g) of piperidine in 50 ml acetonitrile is added dropwise to 0.2 mol (29.1 g) in 5-methyl-4-isoxazolecarboxylic acid chloride, dissolved in 350 ml of acetonitrile, at room temperature with stirring such that the temperature of the reaction solution does not rise above 40° C. Stirring is then continued for 15 minutes and the mixture is subsequently cooled to room temperature.

The piperidine hydrochloride precipitated is filtered off with suction and the filtrate is concentrated under reduced pressure.

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Hoechst Aktiengesellschaft

Patent: US4636513 A1, 1987 ; Title/Abstract

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2:(2)

0.2 mol (17.0 g) of piperidine is added dropwise to 0.1 mol (16.0 g) of 5-ethyl-4-isoxazolecarboxylic acid chloride dissolved in 200 ml of acetonitrile, at room temperature with stirring.

Stirring is continued for 20 minutes and the mixture is then cooled to room temperature and the piperidine hydrochloride precipitated is filtered off with suction.

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E. R. Squibb and Sons, Inc.

Patent: US3966746 A1, 1976 ; Title/Abstract

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2.d:d.

d.

1-Ethyl-3-methyl-4-(1-piperidino)-1H-pyrazolo[3,4-b]pyridine-5-(N-piperidyl)-carboxamide To a solution of 7.7 g of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl chloride (0.03 mol) in 100 ml of dry benzene, 11.2 g of piperidine (0.144 mol) is added dropwise.

The mixture is stirred at 50° (bath temperature) for 3 hours.

After filtering the precipitated piperidine hydrochloride under suction the benzene filtrate is evaporated in vacuo, and the remaining oil is treated with water and then extracted with ether.

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American Hoechst Corporation

Patent: US4031221 A1, 1977 ;

Title/Abstract

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3.b:EXAMPLE 3

The oil is dissolved in 150 ml. of ether, and 50 ml. of a saturated ethereal-HCl solution is slowly added.

The salt precipitates out of solution, is collected, and dried.

The salt is recrystallized from an ethanol and ether mixture to give white needles of the piperidine hydrochloride.

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CIBA-GEIGY AG

Patent: EP744392 A1, 1996 ; Title/Abstract

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1:Example 1

Example 1 : 2,6-Di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone To a solution of 23.7 g (0.28 mol) of piperidine, 106.1 g (1.0 mol) of benzaldehyde and 206.3 g (1.0 mol) of 2,6-di-tert-butylphenol in 20 ml of toluene is added slowly 70 g (0.82 mol) of piperidine over a one-hour period at 135°C-140°C. The reaction mixture is then heated for another three hours with a continuous separation of water occurring.

The resulting Mannich base prepared in situ is diluted with 200 ml of xylene and hydrogen chloride gas is bubbled into the reaction mixture at about 140°C till a state of saturation is reached in about 45 minutes.

The mixture is heated for another hour to ensure that the reaction is complete as seen by thin layer chromatography (tlc) and gas liquid chromatography (glc) tests.

The piperidine hydrochloride formed is removed by filtration.

The dark red filtrate obtained is washed thrice with 200 ml of water and finally stirred with 100 g of Kieselgur for 30 minutes.

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Richter Gedeon Vegyeszeti Gyar R.T.

Patent: EP468825 A1, 1992 ; Title/Abstract

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2:Example 2

Example 2 N-{[dimethyl-(4-fluorobenzyl)-silyl]methyl}piperidine hydrochloride After adding 32.7 g of piperidine to a solution containing 32.5 g of chloromethyl-dimethyl-(4-fluoro-benzyl)-silane in 40 ml of xylene, the reaction mixture is refluxed for 6 hours under stirring, then the precipitated piperidine hydrochloride is filtered at 20 °C and washed in 3 portions with a total of 60 ml of benzene.

The filtrate is combined with the benzene washings and washed in 3 portions with a total of 150 ml of water and the organic phase is dried over anhydrous magnesium sulfate.

A

B

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B

31

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A: 7% B: 77%

32

Stage #1: in diethyl ether

T=20°C; 1.5 h; Stage #2: With acetyl chloride in diethyl ether

T=20°C; 0.333333 h; Further stages.;

Kelly, T. Ross; Lebedev, Rimma L.

Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2197 - 2205 Title/Abstract

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B: 47%

Stage #1: in diethyl ether

T=20°C; 1.5 h; Stage #2: With acetyl chloride in diethyl ether

T=20°C; 0.333333 h;

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Kelly, T. Ross; Lebedev, Rimma L.

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B: 69%

Stage #1: in diethyl ether

T=20°C; 1.5 h; Stage #2: With acetyl chloride in diethyl ether

T=20°C; 0.333333 h;

Kelly, T. Ross; Lebedev, Rimma L.

Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2197 - 2205 Title/Abstract

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Astra Zeneca AB

Patent: US6365602 B1, 2002 ;

Rx-ID: 24091542 Find similar reactions

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20.b:N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[2-methoxycarbonylphenyl]-1-piperidinyl]butyl]-N-methyl-3-cyanonaphthamide Citrate

(b) 4-(2-Methoxycarbonylphenyl)piperidine hydrochloride.

4-(2-Methoxycarbonylphenyl)pyridine hydrochloride (0.595 g) was dissolved in acetic acid (30 mL), platinum dioxide (0.240 g) was added and the mixture shaken under hydrogen (50 psi) for 3 h.

The solution was filtered, acidified with 4M HCl and evaporated to provide the piperidine hydrochloride (0.243 g) as a white solid. MS: m/z 220 (M+H).

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Astra Zeneca AB

Patent: US6365602 B1, 2002 ; Title/Abstract

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34.b:N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[2-trifluoromethylphenyl]-1-piperidinyl]butyl]-N-methyl-3-nitronaphthamide Citrate

(b) 4-(2-Trifluoromethylphenyl)piperidine hydrochloride.

4-(2-Trifluoromethylphenyl)pyridine hydrochloride (0.250 g) was dissolved in acetic acid (15 mL), platinum dioxide (0.100 g) was added and the mixture was shaken under hydrogen (50 psi) for 4 h.

The solution was filtered, acidified with 4N HCl and evaporated to provide the piperidine hydrochloride (0.243 g) as a white solid. MS: m/z 230 (M+H).

1H NMR (DMSO d ) δ 7.71 (m, 2H), 7.57 (d, J=9, 1H), 7.44 (m, 1H), 3.38 (m, 2H), 3.10 (m, 3H), 2.11 (m, 2H), 1.82 (m, 2H).

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A: 0.74 g (48%)

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-n-hexylpiperidine hydrochloride

trans-2-methyl-6-n-hexylpiperidine hydrochloride To a stirred solution of trans-N-Boc-2-methyl-6-n-hexylpiperidine (1.14 g. 4.02 mmol) in 90 ml of CH2Cl2 at 0° C. was added dropwise trifluoroacetic acid (6.6 mL, 85.72 mmol).

The cooling bath was removed, and stirring was continued for 1 h at room temperature.

After concentrating the resulting solution on a rotary evaporator, the remaining liquid was dissolved in ether (40 mL), and 20 ml of water was added.

The aqueous phase was extracted with ether (2*10 mL), and the combined organic extracts were washed with saturated NaHCO3 (2*30 mL) and brine.

The organic phase was dried over K2CO3, filtered through Celite, and concentrated on a rotary evaporator.

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give 0.74 g (48percent) of the piperidinium hydrochloride as white needles. mp 130.7-131.8° C.; 1H NMR (300 MHz) δ9.32 (s, 2H), 3.53 (s, 1H), 3.27 (s, 1H), 2.01-1.26 (m, 19 H), 0.85 (t, 3H); 13C NMR (75 MHz)

δ51.7 (s), 47.9 (s), 31.6 (s), 30.7 (s), 28.92 (s), 28.84 (s), 26.11 (s), 25.72 (s), 22.48 (s), 17.29 (s), 16.83 (s), 13.97 (s). FT-IR: 3489, 2934, 1558, 1540, 1473, 1457, 1299, 1123, 1072, 977, 885, 721.

Elemental Analysis for C12H26NCl: C, 65.58percent; H, 11.92percent; N, 6.37percent. Found: C, 65.60percent; H, 11.86percent; N, 6.27percent.

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A: 0.350 g (55%)

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-cyclopentylpiperidine hydrochloride

trans-2-methyl-6-cyclopentylpiperidine hydrochloride To a stirred solution of trans-N-Boc-2-methyl-6-cyclopentylpiperidine (0.84 g. 3.14 mmol) in 115 ml of CH2Cl2 at 0° C. was added dropwise trifluoroacetic acid (7.3 mL, 94.22 mmol).

The cooling bath was removed, and stirring was continued for 1 h at room temperature.

After concentrating the resulting solution on a rotary evaporator, the remaining liquid was dissolved in ether (40 mL), and 20 ml of water was added.

The aqueous phase was extracted with ether (2*10 mL), and the combined organic extracts were washed with saturated NaHCO3 (2*30 mL) and brine.

The organic phase was dried over K2CO3, filtered through Celite, and concentrated on a rotary evaporator.

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give 0.350 g (55percent) of the piperidinium hydrochloride as white needles. mp 166.0-166.9° C.; 1H NMR (300 MHz) δ9.26-9.0 (br d, 2H), 3.67 (s, 1H), 2.99 (s, 1H), 2.31-1.18 (m, 18H); 13C NMR (75 MHz) δ52.1 (s), 48.3 (s), 31.5 (s).

28.9 (s), 28.9 (s), 26.9 (s), 25.3 (s), 22.4 (s), 20.8 (s). FT-IR (neat): 3420, 2940, 2867, 1652, 1591, 1456, 1428, 1417, 1176, 1120, 1087, 998, 879.

Elemental Analysis for C11H22NCl: C, 64.83percent; H, 10.90percent; N, 6.87percent. Found: C, 64.96percent; H, 10.94percent; N, 6.84percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-(1-isopentenyl)piperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 157.5-156.5° C.; 1H NMR (250 MHz) δ9.37 (br. d, 2H), 5.59-5.46 (m, 2H), 4.19 (s, 1H), 3.59 (s, 1H), 2.66-2.59 (m, 1H), 1.8-1.5 (m, 9H), 1.0 (pair of d, 6H); 13C NMR (62.7 MHz) δ143.6 (s), 120.6 (s), 48.3 (s), 47.9 (s), 28.9 (s), 28.6 (s), 27.3 (s), 23.01 (s), 22.6 (s), 17.5 (s), 16.9 (s). FT-IR (neat): 3426, 3188, 3018, 2952, 1625, 1584, 1464, 1359, 1180, 1099, 958, 881.

Elemental Analysis for C11H22NCl: C, 64.84percent; H, 10.91percent; N, 6.87percent. Found: C, 64.06percent; H, 10.77percent; N, 6.78percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-n-pentylpiperidine hydrochloride

trans-2-methyl-6-n-pentylpiperidine hydrochloride To a stirred solution of trans-N-Boc-2-methyl-6-n-pentylpiperidine (0.77 g. 2.86 mmol) in 90 ml of CH2Cl2 at 0° C. was ad dropwise trifluoroacetic acid (6.6 mL, 85.72 mmol).

The cooling bath was removed, and stirring was continued for 1 h at room temperature.

After concentrating the resulting solution on a rotary evaporator, the remaining liquid was dissolved in ether (40 mL), and 20 ml of water was added.

The aqueous phase was extracted with ether (2*10 mL), and the combined organic extracts were washed with saturated NaHCO3 (2*30 mL) and brine.

The organic phase was dried over K2CO3, filtered through Celite, and concentrated on a rotary evaporator.

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as white needles. mp 109.6-110.9° C.; 1H NMR (300 MHz) δ9.30 (br s, 2 H), 3.53 (br. s, 1 H), 3.27 (br s, 1 H), 1.96-1.29 (m, 17 H), 0.89-0.85 (t, 3 H); 13C NMR (75 MHz) 51.7 (s), 47.9 (s), 31.4 (s), 30.6 (s), 28.8 (s), 28.1 (s), 26.1 (s), 25.4 (s), 24.9 (s), 22.4 (s), 17.3 (s), 16.8 (s). FT-IR: 3421, 2932, 1589, 1458, 1392, 1378, 1357, 1102, 727.

Elemental Analysis for C11H24NCl: C, 64.21percent; H, 11.76percent; N, 6.81percent. Found: C, 64.19percent; H, 11.72percent; N, 6.71percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-n-propylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 124-125.9° C.; 1H NMR (300 MHz) δ9.92 (s, 2H), 3.54 (s, 1H), 3.29 (s, 1H), 2.0-1.2 (m, 13 H), 0.91 (t, 3H); 13C NMR (75 MHz) δ51.38 (s), 47.82 (s), 32.68 (s), 28.73 (s), 26.14 (s), 18.93 (s), 17.24 (s), 16.69 (s), 13.65 (s) ppm. FT-IR (neat): 3409, 2939, 1591, 1433, 1376, 1183, 1067, 993, 881. MS m/z 142, 141, 140, 126, 98, 84, 81, 70, 55, 44, 41.

Elemental Analysis for C9H20NCl: C, 60.81percent; H, 11.36percent; N, 7.88percent. Found: C, 60.72percent; H, 11.30percent; N, 7.82percent.

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A: 1.43 g (71%)

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-butyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give 1.43 g (71percent) of the piperidinium hydrochloride as a white solid. mp 118.0-119.0° C.; 1H NMR (250 MHz) δ9.87 (s, 2H), 3.53 (s, 1H), 3.27 (s, 1H), 2.0-1.2 (m, 15H), 0.90 (t, 3H); 13C NMR (62.7 MHz) δ51.57 (s), 47.78 (s), 30.22 (s), 28.78 (s), 26.05 (s), 22.28 (s), 17.24 (s), 16.78 (s), 13.81 (s) ppm. FT-IR (neat): 3430, 2954, 2925, 1584, 1558, 1456, 1418, 1339, 1028, 1009. MS m/z 156, 155, 154, 140, 98, 84, 81, 70, 55, 44, 41.

Elemental Analysis for C10H22NCl: C, 62.63percent; H, 11.59percent; N, 7.30percent. Found: C, 62.67percent; H, 11.52percent; N, 7.34percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-heptyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 123-125° C.; 1H NMR (250 MHz) δ9.29 (s, 2H), 3.51 (s, 1H), 3.25 (s, 1H), 2.0-1.2 (m, 21H), 0.85 (t, 3H); 13C NMR (62.7 MHz) 51.7 (s), 47.9 (s), 31.7 (s), 30.7 (s), 29.2 (s), 2.91 (s), 28.8 (s), 26.1 (s), 25.8 (s), 22.5 (s), 17.3 (s), 16.8 (s), 14.0 (s) ppm. FT-IR (neat): 3420, 2956, 2919, 1587, 1470, 1463, 1454, 1393, 1360, 1184, 1125, 890.

Elemental Analysis for C13H28NCl: C, 66.76percent; H, 12.09percent; N, 5.99percent. Found: C, 66.58percent; H, 12.06percent; N, 6.01percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-(2-phenylethyl)piperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 148.3-151.0; 1H-NMR (300 MHz) δ9.3, (s, 2H), 7.28-7.11 (m, 5H), 3.43 (s, 1H), 3.19 (s, 1H), 2.67-1.27 (m, 13H); 13C NMR (75 MHz) 140.0 (s), 128.3 (s), 126.1 (s), 50.9 (s), 47.9 (s), 32.1 (s), 31.5 (s), 28.5 (s), 26.4 (s), 17.2 (s), 16.5 (s). FT-IR (neat): 3410, 3075, 2944, 1590, 1494, 1454, 1435, 1336, 1122, 1029, 751, 701.

Elemental Analysis for C14H22NCl: C, 70.11percent; H, 9.27percent; N, 5.84percent. Found: C, 69.95percent; H, 9.19percent; N, 5.79percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-ethyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 174.9-175.2° C.; 1H NMR (250 MHz) δ9.33 (s, 2H), 3.54 (s, 1H), 3.19 (s, 1H), 2.07-1.46 (m, 13H), 0.99 (t, 3H); 13C NMR (62.7 MHz) 53.0 (s), 47.9 (s), 28.8 (s), 25.6 (s), 2.38 (s), 17.2 (s), 16.8 (s), 10.2 (s) ppm. FT-IR (neat): 3420, 2931, 1588, 1455, 1393, 1186, 1065, 960.

Elemental Analysis for C8H18NCl: C, 58.69percent; H, 11.11percent; N, 8.55percent. Found: C, 58.64percent; H, 11.09percent; N, 8.56percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-(1-propenyl)piperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid that was homogeneous by TLC analysis. mp 139.5-141.1° C.; 1H NMR (250 MHz) δ9.39 (s, 2H), 5.84-5.86 (m, 2H), 4.23 (s, 1H), 3.54 (s, 1H), 1.9-1.44 (m, 12H); 13C NMR (62.7 MHz) 131 (s), 123 (s), 48 (s), 28.5 (s), 28 (s), 17.6 (s), 17.1 (s), 13.7 (s) ppm. FT-IR (neat): 3420, 3020, 2944, 1588, 1459, 1434, 1386, 821, 816, 804.

Elemental Analysis for C9H18NCl: C, 61.52percent; H, 10.35percent; N, 7.97percent. Found: C, 61.44percent; H, 10.29percent; N, 7.88percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-(1-butenyl)-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid that was homogeneous by TLC analysis. mp 167-169.0° C.; 1H NMR (250 MHz) δ9.4 (s, 2H), 5.71-5.58 (m, 2H), 4.17 (s, 1H), 3.54 (s, 1H), 2.2-1.4 (m, 11H), 0.98(t, 3H); 13C NMR (62.7 MHz) δ138.5 (s), 122.4 (s), 48.2 (s), 47.9 (s), 28.74 (s), 28.45 (s), 21.3 (s), 17.6 (s), 16.9 (s), 13.8 (s). FT-IR (neat): 3425, 3183, 3072, 2961, 2915, 1656, 1585, 1463, 1443, 1407, 1107, 1075, 960, 883, 803.

Elemental Analysis for C10H20NCl: C, 63.29percent; H, 10.65percent; N, 7.38percent. Found: C, 63.14percent; H, 10.58percent; N, 7.32percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-(1-pentenyl)-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid that was homogeneous by TLC analysis. mp 150.4-150.9° C.; 1H NMR (250 MHz) δ9.5-9.3 (br. d, 2H), 5.74-5.62 (m, 2H), 4.19 (s, 1H), 3.55 (s, 1H), 2.1-1.3 (m, 13H), 0.87 (t, 3H); 13C NMR (62.7 MHz) δ136.8 (s), 123.0 (s), 48.3 (s), 47.9 (s), 29.9 (s), 28.8 (s), 28.4 (s), 22.3 (s), 17.6 (s), 17.1 (s), 13.8 (s). FT-IR (neat): 3424, 3171, 2939, 1635, 1597, 1582, 1459, 1432, 1384, 1287, 1123, 1075, 895.

Elemental Analysis for C11H22NCl: C, 64.83percent; H, 10.9percent; N, 6.87percent. Found: C, 64.77percent; H, 10.82percent; N, 6.85percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-isopentylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 134.1-134.7° C.; 1H NMR (250 MHz) 67 9.36 (s, 2H), 3.53 (s, 1H), 3.25 (s, 1H), 1.96-1.1 (m, 14H), 0.88-0.82 (d, 6H); 13C NMR (62.7 MHz) δ51.9 (s), 47.8 (s), 34.7 (s), 28.9 (s), 28.4 (s), 27.8 (s), 26.0 (s), 22.7 (s), 22.1 (s), 17.3 (s), 16.9 (s). FT-IR (neat): 3422, 2949, 1636, 1602, 1587, 1500, 1422, 1384, 1230, 1105, 1030, 998, 895.

Elemental Analysis for C11H24NCl: C, 64.20percent; H, 11.78percent; N, 6.80percent. Found: C, 64.08percent; H, 11.72percent; N, 6.78percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-isohexyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 155.0-156.0° C.; 1H NMR (250 MHz) δ9.17 (s, 2H), 3.50 (s, 1H), 3.25 (s, 1H), 1.94-1.15 (m, 16H), 0.82 (d, 6H); 13C NMR (62.7 MHz) δ51.7 (s), 47.9 (s), 38.4 (s), 30.9 (s), 28.8 (s), 27.8 (s), 26.1 (s), 23.5 (s), 22.5 (s), 22.3 (s), 17.3 (s), 16.8 (s) ppm. FT-IR (neat): 3430, 2948, 1615, 1589, 1557, 1472, 1436, 1418, 1362, 1102, 895.

Elemental Analysis for C12H26NCl: C, 65.56percent; H, 11.95percent; N, 6.37percent. Found: C, 64.90percent; H, 11.89percent; N, 6.26percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-isohexenyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 164.2-167.0° C.; 1H NMR (250 MHz) δ9.44 (s, 2H), 5.71 (s, 2H), 4.18 (s, 1H), 3.56 (s, 1H), 2.0-1.5 (m, 12H), 0.94 (dd, 6H); 13C NMR (62.7 MHz) δ135.7 (s), 123.6 (s), 4.84 (s), 47.9 (s), 36.9 (s), 28.9 (s), 28.4 (s), 28.2 (s), 22.5 (s), 22.1 (s), 17.6 (s), 17.2 (s) ppm. FT-IR (neat): 3429, 3165, 2940, 1620, 1550, 1478, 1400, 1354, 1097, 890.

Elemental Analysis for C12H24NCl: C, 66.17percent; H, 11.13percent; N, 6.43percent. Found: C, 66.25percent; H, 11.05percent; N, 6.50percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-heptenyl-6-methylpiperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 121.1-122.0° C.; 1H NMR(CDCl3) δ9.44 (s, 2H), 5.68 (m, 2H), 4.19 (s, 1H), 3.56 (s, 1H), 2.2-1.2 (m, 17H), 0.88 (t, 3H); 13C NMR (CDCl3) δ137.1 (s), 122.8 (s),

48.34 (s, 1H), (s), 31.4 (s), 28.8 (s), 28.4 (s), 27.9 (s), 22.4 (s), 17.6 (s), 17.1 (s), 13.97 (s). FT-IR (near): 3435, 3192, 2924, 1586, 1431, 1030, 673.

Elemental Analysis for C13H26NCl: C, 67.34percent; H, 11.33percent; N, 6.04percent. Found: C, 67.44percent; H, 11.23percent; N, 5.98percent.

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52

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-(ethyl propionyl)piperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 121.1-122.0° C.; 1H NMR (300 MHz) δ9.44 (s, 2H), 5.68 (m, 2H), 4.19 (s, 1H), 3.56 (s, 1H), 2.2-1.2 (m, 17H), 0.88 (t, 3H); 13C NMR (75 MHz) δ137.1 (s), 122.8 (s), 48.34 (s), 47.94 (s), 31.4 (s), 28.8 (s), 28.4 (s), 27.9 (s), 22.4 (s), 17.6 (s), 17.1 (s), 13.97 (s) ppm. FT-IR (neat): 3435, 3192, 2924, 1586, 1431, 1030, 673.

Elemental Analysis. for C13H26NCl: C, 67.34percent; H, 11.33percent; N, 6.04percent. Found: C, 67.44percent; H, 11.23percent; N, 5.98percent.

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Bowen, J. Phillip; Furness, M. Scott; Whitmire, David

Patent: US6369078 B1, 2002 ; Title/Abstract

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trans-2-methyl-6-(ethenyl propionyl)piperidine hydrochloride

The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette.

This solution was allowed to stand for 10 minutes, and the solvent was evaporated.

More ether was added and the flask was swirled constantly until crystallization occured.

The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 154.8-156.3; 1H NMR (300 MHz) δ9.89 (s, 2H), 7.03 (dd, 1H), 6.24 (d, 1H), 4.24-4.11 (m, 3H), 3.45 (s, 1H), 2.2-1.49 (m, 9H), 1.26-1.22 (t, 3H); 13C NMR (75 MHz) δ165.1 (s), 140.1 (s), 126.3 (s), 60.83 (s), 54.3 (s), 51.8 (s), 48.6 (s), 29.4 (s), 27.9 (s), 26.3 (s), 17.9 (s), 14.1 (s) ppm. FT-IR (neat): 3374, 3107, 2943, 1717, 1683, 1635, 1539, 1436, 1312, 1190, 1033, 981.

Elemental Analysis for C11H20NO2Cl: C, 56.52percent; H, 8.64percent; N, 5.99percent. Found: C, 56.37percent; H, 8.58percent; N, 5.89percent.

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With hydrogenchloride; methanol; lithium triethylborohydride

1.) THF, RT. 0.5 h; Yield given. Multistep reaction;

Blough; Carroll

Tetrahedron Letters, 1993 , vol. 34, # 45 p. 7239 - 7242 Title/Abstract

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95 % Spectr.

Stage #1: With ammonium formate; 10percent palladium on carbon in methanol

T=20°C; 16 h; Stage #2: With hydrogenchloride in methanol

Further stages.;

Zacharie; Moreau; Dockendorff

Journal of Organic Chemistry, 2001 , vol. 66, # 15 p. 5264 - 5265 Title/Abstract

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100%

Stage #1: With ammonium formate; 10percent palladium on carbon in methanol

T=20°C; 16 h; Stage #2: With hydrogenchloride in methanol

Further stages.;

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Rx-ID: 8864253 Find similar reactions

Zacharie; Moreau; Dockendorff

Journal of Organic Chemistry, 2001 , vol. 66, # 15 p. 5264 - 5265 Title/Abstract

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56

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Rx-ID: 27205484 Find similar reactions

A: 78%

in acetonitrile

to suspn. PdCl2(dipy) in CH3CN was added piperidine (1:2), suspn. was allowed to react under stirring with CO (0.1 MPa) at room temp. for 3 h; filtered off, washed with CH3CN/CH3OH (10:1), and dried in vacuo; elem.anal.;

Aresta, Michele; Giannoccaro, Potenzo; Tommasi, Immacolata; Dibenedetto, Angela; Lanfredi, Anna Maria Manotti; Ugozzoli, Franco

Organometallics, 2000 , vol. 19, # 19 p. 3879 - 3889 Title/Abstract

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A: 72%

in acetonitrile

to suspn. PdCl2(dipy) in MeCN was added piperidine (1:10), mixt. was reacted with CO (0.1 MPa) at room temp. for 2 h; mixt. was concd. and filtered; elem. anal.;

Aresta, Michele; Giannoccaro, Potenzo; Tommasi, Immacolata; Dibenedetto, Angela; Lanfredi, Anna Maria Manotti; Ugozzoli, Franco

Organometallics, 2000 , vol. 19, # 19 p. 3879 - 3889 Title/Abstract

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58

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Rx-ID: 27205486 Find similar reactions

A: 80%

in acetonitrile

to suspn. PdCl2(phen) in CH3CN was added piperidine (1:2), suspn. was allowed to react under stirring with CO (0.1 MPa) at 313 K for 3 h; filtered off, washed with CH3CN/CH3OH (10:1), and dried in vacuo; elem.anal.;

Aresta, Michele; Giannoccaro, Potenzo; Tommasi, Immacolata; Dibenedetto, Angela; Lanfredi, Anna Maria Manotti; Ugozzoli, Franco

Organometallics, 2000 , vol. 19, # 19 p. 3879 - 3889 Title/Abstract

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A

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59

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A: 70%

60

in acetonitrile

to suspn. PdCl2(phen) in MeCN was added piperidine (1:10), mixt. was reacted with CO (0.1 MPa) at room temp. for 4 h; mixt. was concd. and filtered; elem. anal.;

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Aresta, Michele; Giannoccaro, Potenzo; Tommasi, Immacolata; Dibenedetto, Angela; Lanfredi, Anna Maria Manotti; Ugozzoli, Franco

Organometallics, 2000 , vol. 19, # 19 p. 3879 - 3889 Title/Abstract

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With hydrogenchloride; chloroformic acid vinyl ester

various substituted piperidines; Product distribution;

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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With hydrogenchloride; chloroformic acid vinyl ester

1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.) MeOH, 50-60 deg C, 4.5 h; Yield given. Multistep reaction;

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 1 h / Heating 2: 99 percent / methanol / 0.5 h / 50 °C View Scheme

Olofson, R. A.; Martz, Jonathan T.; Senet, Jean-Pierre; Piteau, Marc; Malfroot, Thierry

Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2081 - 2082 Title/Abstract

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61

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With hydrogenchloride; chloroformic acid vinyl ester

1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.) MeOH, 50-60 deg C, 4.5 h; Yield given. Multistep reaction;

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Rx-ID: 4985897 Find similar reactions

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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62

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Multi-step reaction with 3 steps 1: 87 percent / NaOH / H2O / 1 h 2: 83 percent / LiAlH4 / diethyl ether / Heating 3: 1.) vinyl chloroformate, 2.) HCl / 1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.)

MeOH, 50-60 deg C, 4.5 h View Scheme

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Rx-ID: 16696067 Find similar reactions

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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63

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Multi-step reaction with 2 steps 1: 85 percent / LiAlH4 / diethyl ether / Heating 2: 1.) vinyl chloroformate, 2.) HCl / 1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.)

MeOH, 50-60 deg C, 4.5 h View Scheme

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Rx-ID: 16698187 Find similar reactions

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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64

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Multi-step reaction with 2 steps 1: 83 percent / LiAlH4 / diethyl ether / Heating 2: 1.) vinyl chloroformate, 2.) HCl / 1.) CH2Cl2, 0 deg C to room temperature;reflux, 4 h, 3.)

MeOH, 50-60 deg C, 4.5 h View Scheme

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Rx-ID: 16699045 Find similar reactions

Howarth, Nicola M.; Malpass, John R.; Smith, Craig R.

Tetrahedron, 1998 , vol. 54, # 36 p. 10899 - 10914 Title/Abstract

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65

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Rx-ID: 24573270 Find similar reactions

With hydrogenchloride in methanol; ethyl acetate

Merck and Co., Inc.

Patent: US5492920 A1, 1996 ;

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Title/Abstract

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44:EXAMPLE 44 STR122

This material was dissolved in methanol and 5 mL of saturated HCl in ethyl acetate was added and concentrated to give the hydrochloride salt.

To 2 g of the above pyridine hydrochloride salt in 15 mL of methanol was added 0.225 g of platinum oxide and hydrogenated at 50 psi on the Parr shaker for 2 h.

The catalyst was filtered off through a pad of celite and washed with methanol.

The filtrate was concentrated to give 2.17 of the piperidine hydrochloride as a foam. STR123 The title compound was prepared from the compound made in Step A and Intermediate 3 as described previously.

1 H NMR (400 MHz, CD OD mixture of rotamers): 8.10 (t, 1H), 7.78 (dd, 1H), 7.50-7.00 (m, 8H), 4.90 (m, 1H), 4.55 (d, 1H), 3.94 and 3.90 (2 doublets, 1H), 3.85 (s, 3H), 3.80-3.60 (m, 1H), 3.05 (dt, 1H), 2.70-2.50 (m, 4H), 1.90-1.50 (m, 6H), 1.55 (s, 3H), 1.50 9s, 3H), 1.40 3

(m, 1H).

With hydrogenchloride in methanol; ethyl acetate

Merck and Co., Inc.

Patent: US5721251 A1, 1998 ;

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Title/Abstract

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44:EXAMPLE 44 STR125

This material was dissolved in methanol and 5 mL of saturated HCl in ethyl acetate was added and concentrated to give the hydrochloride salt.

To 2 g of the above pyridine hydrochloride salt in 15 mL of methanol was added 0.225 g of platinum oxide and hydrogenated at 50 psi on the Parr shaker for 2 h.

The catalyst was filtered off through a pad of celite and washed with methanol.

The filtrate was concentrated to give 2.17 of the piperidine hydrochloride as a foam. STR126 The title compound was prepared from the compound made in Step A and Intermediate 3 as described previously. 1 H NMR (400 MHz, CD3 OD mixture of rotamers): 8.10 (t, 1H), 7.78 (dd, 1H), 7.50-7.00 (m, 8H), 4.90 (m, 1H), 4.55 (d, 1H), 3.94 and 3.90 (2 doublets, 1H),

3.85 (s, 3H), 3.80-3.60 (m, 1H), 3.05 (dt, 1H), 2.70-2.50 (m, 4H), 1.90-1.50 (m, 6H), 1.55 (s, 3H), 1.50 9s, 3H), 1.40 (m, 1H).

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A: 91.5 g (73%)

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Merck and Co., Inc.

Patent: US5830433 A1, 1998 ; Title/Abstract

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3:1,2-Dihydro-1-benzyloxycarbonyl-spiro[3H-indole-3,4'-piperdine] hydrochloride

A solution of the above piperidine (91.26 g) in 1000 mL of ethyl acetate containing a trace of methanol was treated with dry HCl (gas) till the reaction mixture was acidic.

The reaction mixture was concentrated to dryness and the foamy residue was triturated with ether to give 91.5 g (73percent) of the subject piperidine hydrochloride salt as a pale yellow solid.

67

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With boron trichloride in dichloromethane

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Rx-ID: 3453678 Find similar reactions

Jego, J. M.; Carboni, B.; Vaultier, M.

Bulletin de la Societe Chimique de France, 1992 , # 6 p. 554 - 565 Title/Abstract

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68

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in toluene

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Ciba-Geigy Corporation

Patent: US5059689 A1, 1991 ; Title/Abstract

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10:EXAMPLE 10

EXAMPLE 10 2,4-Dichloro-6-(2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl)-1,3,5-triazine.

62.7 g of 4-hexyloxy-2,2,6,6-tetramethylpiperidine are added with stirring to a solution of 23.9 g of cyanuric chloride in 100 ml of toluene.

The mixture is subsequently heated to 80° for 24 hours.

A white precipitate of the piperidine hydrochloride is formed during this.

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69

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Rx-ID: 1482391 Find similar reactions

in acetonitrile

T=10°C; temperature, deuterated compound, isotope effect, ΔH(excit.), ΔS(excit.), ΔG(excit.); KineticsThermodynamic data;

Dworniczak, Miroslaw; Jarczewski, Arnold

Acta Chimica Hungarica, 1989 , vol. 126, # 5 p. 599 - 604 Title/Abstract

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70

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Rx-ID: 3719842 Find similar reactions

Yield given. Multistep reaction;

Jego, Jean Michel; Carboni, Bertrand; Vaultier, Michel; Carrie, Robert

Journal of the Chemical Society, Chemical Communications, 1989 , # 2 p. 142 - 143 Title/Abstract

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71

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in methanol; acetone

react. of Ru complex suspn. (methanol/acetone) with piperidine, at room temp., 5h or at 60°C, 30 min.; color change to yellowish orange; evapn.; all operations under inert gas; extraction (benzene);

Dieck, Heihdirk Tom; Kleinwaechter, Ingo; Haupt, Erhard T. K.; Bolze-Kuhrt, Doerte

Journal of Organometallic Chemistry, 1989 , vol. 365, p. 351 - 362 Title/Abstract

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72

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79%

in dichloromethane

to soln. of azide was added soln. of BCl3 at -78°C; mixt. was allowed to warm up to room temp. overnight, MeOH added and solvents removed; characterized as benzoyl deriv.;

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Jego, Jean Michel; Carboni, Bertrand; Vaultier, Michel; Carrie, Robert

Journal of the Chemical Society, Chemical Communications, 1989 , # 2 p. 142 - 143 Title/Abstract

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A

73

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Rx-ID: 1482772 Find similar reactions

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in acetonitrile

T=25°C; Rate constant;

Kolesnikova, I. V.; Petrova, T. D.; Platonov, V.E.; Mikhailov, V. A.; Popov, A. A.; Savelova, V.A.

Journal of Fluorine Chemistry, 1988 , vol. 40, p. 217 - 246 Title/Abstract

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in acetonitrile

T=25°C;

Kolesnikova, I. V.; Petrova, T. D.; Platonov, V.E.; Mikhailov, V. A.; Popov, A. A.; Savelova, V.A.

Journal of Fluorine Chemistry, 1988 , vol. 40, p. 217 - 246 Title/Abstract

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A

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74

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Rx-ID: 1484601 Find similar reactions

With acetic acid in cyclohexane

T=30°C;

Popov, A. F.; Anikeev, A. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 939 - 944 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1040 - 1046 Title/Abstract

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With acetic acid in cyclohexane

T=30°C; other concentrations, other catalyst; Rate constantMechanism;

Popov, A. F.; Anikeev, A. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 939 - 944 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1040 - 1046 Title/Abstract

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75

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in acetonitrile

T=25°C; Rate constant;

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Titskii, G. D.; Mitchenko, E. S.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 10 p. 1949 - 1954 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 10 p. 2161 - 2166 Title/Abstract

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76

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Rx-ID: 1486431 Find similar reactions

B: 98%

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Marchenko, A. P.; Shaposhnikov, S. I.; Koidan, G. N.; Kharchenko, A. V.; Pinchuk, A. M.

J. Gen. Chem. USSR (Engl. Transl.), 1988 , vol. 58, # 10 p. 2230 - 2237,1985 - 1992 Title/Abstract

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6 h;

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77

B: 70%

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Rx-ID: 25001129 Find similar reactions

Societe Nationale des Poudres et Explosifs

Patent: US4725680 A1, 1988 ; Title/Abstract

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25.b:(b)

(b) Reaction of α-chloroethoxycarbonylimidazole with piperidine A solution of 8.5 g (0.1 mole) of piperidine in 10 ml of THF is added dropwise to a solution of α-chloroethoxycarbonylimidazole (8.75 g; 0.05 mole) in 50 ml of THF. This solution is cooled to +5° C. while the addition is taking place, and then stirred at room temperature.

The piperidine hydrochloride formed is filtered off and the organic phase then washed once with water.

After this is dried over magnesium sulphate and the solvent evaporated, the residual mixture is distilled and 6.2 g (yield: 70percent) of the expected product is recovered.

B.p. 134° C./26.6 Pa (0.2 mm Hg).

The liquid obtained crystallises spontaneously in the refrigerator.

M.p. 38° C. 1 H NMR: 1.5 ppm multiplet (CH ) ; 3.5 ppm multiplet STR58 2 3

IR: νC=0 1690 cm-1.

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B

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C

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Rx-ID: 2425954 Find similar reactions

in chloroform

96 h; Heatingvar. time; Equilibrium constant;

Doomes, Earl; Overton, Belinda M.

Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1544 - 1548 Title/Abstract

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79

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Rx-ID: 2426059 Find similar reactions

in chloroform

72 h; Heating; Equilibrium constant;

Doomes, Earl; Overton, Belinda M.

Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1544 - 1548 Title/Abstract

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80

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B: 77% C: 100%

With N-chlorothiophthalimide in 1,2-dichloroethane

T=20 - 25°C; 2 h;

Borovikova, G.S.; Levchenko, E.S.; Kaminskaya, E.I.

Journal of Organic Chemistry USSR (English Translation), 1986 , vol. 22, p. 86 - 92 Zhurnal Organicheskoi Khimii, 1986 , vol. 22, # 1 p. 100 - 106 Title/Abstract

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A

81

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With hydrogenchloride

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Keiko, N. A.; Rulev, A. Yu.; Khalikhman, I. D.; Voronkov, M. G.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986 , vol. 35, # 11 p. 2260 - 2262 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986 , # 11 p. 2471 - 2474 Title/Abstract

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A

B

C

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82

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Rx-ID: 1481715 Find similar reactions

A: 11% C: 42%

T=100°C; 4 h;

Ganin, E. V.; Makarov, V. F.; Rozynov, B. V.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, # 11 p. 2205 - 2208 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 11 p. 2411 - 2415 Title/Abstract

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A: 11% C: 42%

T=100°C; 4 h;

Ganin, E. V.; Makarov, V. F.; Rozynov, B. V.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, # 11 p. 2205 - 2208 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 11 p. 2411 - 2415 Title/Abstract

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83

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Rx-ID: 1486747 Find similar reactions

50%

With tetrachloromethane; dicarbonylchloro(2,1,3benzothiadiazole)rhodium(I)

360 h; Ambient temperaturealso with other chlorinated solvents and rhodium complex catalysts;

Krylov, V. K.; Kukushkin, Yu. N.; Dushina, M. E.

J. Gen. Chem. USSR (Engl. Transl.), 1985 , vol. 55, # 10 p. 2400,2133 Title/Abstract

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Multi-step reaction with 2 steps 1: 18 percent / CHCl3 / 8 h / Heating 2: 0.4 g / HCl / diethyl ether View Scheme

Protiva; Sindelar; Valenta; et al.

Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 11 p. 3094 - 3113 Title/Abstract

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A

B

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84

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B: 15%

With piperidine in acetonitrile

2 h; Heating;

Einbaum, Priit; Suschitzky, Hans

Phosphorus and Sulfur and the Related Elements, 1985 , vol. 22, p. 231 - 240 Title/Abstract

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B: 15%

With piperidine in acetonitrile

2 h; Heatingreactions with var. Nnucleophiles; Product distribution;

Einbaum, Priit; Suschitzky, Hans

Phosphorus and Sulfur and the Related Elements, 1985 , vol. 22, p. 231 - 240 Title/Abstract

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A

B

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85

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B: 99%

With piperidine in tetrahydrofuran

0.166667 h; Ambient temperature;

Einbaum, Priit; Suschitzky, Hans

Phosphorus and Sulfur and the Related Elements, 1985 , vol. 22, p. 231 - 240 Title/Abstract

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86

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99%

With methanol

T=50°C; 0.5 h;

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Rx-ID: 1716497 Find similar reactions

Olofson, R. A.; Martz, Jonathan T.; Senet, Jean-Pierre; Piteau, Marc; Malfroot, Thierry

Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 2081 - 2082 Title/Abstract

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A

B

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87

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With hydrogenchloride

0.0833333 h;

Souizi, A.; Robert, A.

Tetrahedron, 1984 , vol. 40, # 10 p. 1817 - 1822 Title/Abstract

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88

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Multi-step reaction with 2 steps 1: NaBD4 / ethanol / 15 h 2: HCl / 0.08 h View Scheme

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Rx-ID: 20767469 Find similar reactions

Souizi, A.; Robert, A.

Tetrahedron, 1984 , vol. 40, # 10 p. 1817 - 1822 Title/Abstract

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89

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88%

With hydrogenchloride

T=70°C; 1 h; acid degradation;

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Rx-ID: 1771999 Find similar reactions

Zhao, Yu-Fen; Ji, Gai-Jiao; Xi, She-Kang; Tang, Hue-Gong; Song, Ai-Teng; Wei, Shou-Zuo

Phosphorus and Sulfur and the Related Elements, 1983 , vol. 18, p. 155 - 158 Title/Abstract

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A

B

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90

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Rx-ID: 1482241 Find similar reactions

in hexane

T=25°C; other solvents; Rate constant;

Litvinenko, L. M.; Kravchenko, V. V.; Popov, A. F.; Kostenko, L. I.

Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 7 p. 1324 - 1328 Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 7 p. 1516 - 1520 Title/Abstract

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91

Synthesize Find similar Rx-ID: 1482337 Find similar reactions

in hexane

T=25°C; other solvents; Rate constant;

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Litvinenko, L. M.; Kravchenko, V. V.; Popov, A. F.; Kostenko, L. I.

Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 7 p. 1324 - 1328 Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 7 p. 1516 - 1520 Title/Abstract

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B

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92

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Rx-ID: 1482343 Find similar reactions

in hexane

T=25°C; other solvents; Rate constant;

Litvinenko, L. M.; Kravchenko, V. V.; Popov, A. F.; Kostenko, L. I.

Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 7 p. 1324 - 1328 Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 7 p. 1516 - 1520 Title/Abstract

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A

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93

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Rx-ID: 1482837 Find similar reactions

in hexane

T=25°C; other solvents; Rate constant;

Litvinenko, L. M.; Kravchenko, V. V.; Popov, A. F.; Kostenko, L. I.

Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 7 p. 1324 - 1328 Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 7 p. 1516 - 1520 Title/Abstract

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94

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76%

With 2,3,11,12-dicyclohexano-1,4,7,10,13,16hexaoxacyclo-octadecane in diethylene glycol dimethyl ether

3 h; Ambient temperature;

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Rx-ID: 1657442 Find similar reactions

Ohsawa; Takagaki; Ikehara; et al.

Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 9 p. 3178 - 3186 Title/Abstract

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95

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Rx-ID: 1873711 Find similar reactions

A: 0.4 g B: 0.9 g

With hydrogenchloride in diethyl ether

Protiva; Sindelar; Valenta; et al.

Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 11 p. 3094 - 3113 Title/Abstract

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96

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82%

With 2,3,11,12-dicyclohexano-1,4,7,10,13,16hexaoxacyclo-octadecane in diethylene glycol dimethyl ether

3 h; Ambient temperature;

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Rx-ID: 2045078 Find similar reactions

Ohsawa; Takagaki; Ikehara; et al.

Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 9 p. 3178 - 3186 Title/Abstract

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B

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97

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Rx-ID: 25267080 Find similar reactions

in N-methyl-acetamide

Hide Experimental Procedure

Yamanouchi Pharmaceutical Co., Ltd.

Patent: US3951962 A1, 1976 ; Title/Abstract

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34:EXAMPLE 34

EXAMPLE 34 In 13 ml of dimethylformamide was dissolved 1.904g of tetracycline hydrochloride and after adding 1.224g of 3-piperidino-2-pentene to the solution, the mixture was stirred for 3 hours at room temperature.

After the reaction was over, piperidine hydrochloride precipitated in the reaction was filtered off and the solvent was distilled away from the filtrate.

When 3 ml of water was added to the residue, 1.3g of crystalline N-(1-ethyl-1-propenyl)tetracycline was obtained. in N-methyl-acetamide

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Yamanouchi Pharmaceutical Co., Ltd.

Patent: US3991111 A1, 1976 ; Title/Abstract

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34:EXAMPLE 34:

EXAMPLE 34: In 13 ml of dimethylformamide was dissolved 1.904g of tetracycline hydrochloride and after adding 1.224g of 3-piperidino-2-pentene to the solution, the mixture was stirred for 3 hours at room temperature.

After the reaction was over, piperidine hydrochloride precipitated in the reaction was filtered off and the solvent was distilled away from the filtrate.

When 3 ml of water was added to the residue, 1.3g of crystalline N-(1-ethyl-1-propenyl)tetracycline was obtained.

A

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98

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A: >99 B: >99

With calcium chloride in methanol

byproducts: CaF2, HCl;

Fedotova, L. A.; Voronkov, M. G.

Zhurnal Analiticheskoi Khimii, 1967 , vol. 22, p. 1210 - 1211 Zhurnal Analiticheskoi Khimii, 1967 , vol. 22, p. 1431 - 1433 Full Text Show Details

A: >99 B: >99

With CaCl2 in methanol

byproducts: CaF2, HCl;

Gmelin Handbook: B: B-Verb.4, 4.4.1, page 110 - 117 Full Text Show Details

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99

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Rx-ID: 5581102 Find similar reactions

T=-15°C;

Boehme et al.

Chemische Berichte, 1958 , vol. 91, p. 340,344 Full Text Show Details

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