1.2 Piperidine by Asch

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Citations (573)

Conditions

References A

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100

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Hoechst Marion Roussel, Inc.

Patent: US6004982 A1, 1999 ; Title/Abstract Full Text Show Details

EXAMPLE 1D STR9 Intermediate: 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine

EXAMPLE 1D STR9 Intermediate: 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine 4-[2-(2,3-dimethoxyphenyl)-1-hydroxyethyl]pyridine (20.0 g, 0.077 mol) in acetic acid (170 ml) over 1.5 g of PtO2 was hydrogenated for 45 minutes on a Parr shaker. The reaction was filtered through Celite and filtrate combined with another run of 21.0 g (0.08 mol). The combined filtrates were concentrated in vacuo and the resulting oil was diluted with water. The aqueous solution was made basic with 50percent aqueous NaOH, and the basic mixture extracted with EtOAc. The organic extract was washed with water, dried (magnesium sulfate) and then concentrated to afford 34.3 g of an oil that solidified upon standing. The solid was removed and recrystallized twice from isopropyl ether at 5° C. to afford the piperidine as a white solid, mp 82-84° C. Analysis: Calculated for C15 H23 NO3: 67.90percent C, 8.74percent N. 5.28percent N. Found: 67.92percent C, 8.77percent H, 5.21percent N.

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Aventis Pharmaceuticals Inc.

Patent: EP1015446 B1, 2003 ;

Title/Abstract Full Text Show Details

1.D:Intermediate: 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine EXAMPLE 1D Intermediate: 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine 4-[2-(2,3-dimethoxyphenyl)-1-hydroxyethyl]pyridine (20.0 g, 0.077 mol) in acetic acid (170 ml) over 1.5 g of PtO2 was hydrogenated for 45 minutes on a Parr shaker. The reaction was filtered through Celite and filtrate combined with another run of 21.0 g (0.08 mol). The combined filtrates were concentrated in vacuo and the resulting oil was diluted with water. The aqueous solution was made basic with 50percent aqueous NaOH, and the basic mixture extracted with EtOAc. The organic extract was washed with water, dried (magnesium sulfate) and then concentrated to afford 34.3 g of an oil that solidified upon standing. The solid was removed and recrystallized twice from isopropyl ether at 5°C to afford the piperidine as a white solid, mp 82-84°C.

101

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With hydrogen; palladium on activated charcoal in methanol

T=20°C; 16 h;

Rx-ID: 9054103 Find similar reactions

Schwinn, Dominik; Bannwarth, Willi

Helvetica Chimica Acta, 2002 , vol. 85, # 1 p. 255 - 264 Title/Abstract Full Text View citing articles Show Details

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102

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Rx-ID: 9380353 Find similar reactions

With Cs-P-Si mixed-oxide

T=300°C; P=61504.9 Torr; Further byproducts given. Title compound not separated from byproducts;

Oku, Tomoharu; Ikariya, Takao

Angewandte Chemie - International Edition, 2002 , vol. 41, # 18 p. 3476 - 3479 Title/Abstract Full Text View citing articles Show Details

103

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B: 76%

With tetraethylammonium p-toluenesulfonate

Electrochemical reactionreticulated vitreous carbon anode; Pt cathode;

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D'Oca, Marcelo G. Montes; Russowsky, Dennis; Canto, Karen; Gressler, Tanara; Goncalves, Reinaldo S.

Organic Letters, 2002 , vol. 4, # 10 p. 1763 - 1766 Title/Abstract Full Text View citing articles Show Details

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104

Rx-ID: 24005601 Find similar reactions

Revesz, Laszlo; Schlapbach, Achim

Patent: US2002/49220 A1, 2002 ;

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18.a:a

The combined organic phases are washed with water, dried over Na2SO4, filtered and evaporated to dryness and yielded the piperidine NH analogue of the title compound (177 mg; 0.52 mmol; 8percent), which is treated with (BOC)2O (150 mg; 0.68 mmol) in THF (2 ml) for 1 h at room temperature. The reaction mixture is evaporated to yield the title compound as a colorless foam (270 mg), which is directly used for the next step without purification.

105

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With thionyl chloride; triethylamine in tetrahydrofuran; hydrochlorid acid; dichloromethane; toluene

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Njoroge, F. George; Vibulbhan, Bancha; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Zhu, Hugh Y.; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.

Patent: US2002/198216 A1, 2002 ; Title/Abstract Full Text Show Details

P.34:Preparative Example 34

Preparative Example 34 To a stirred solution of alcohol (280) from Preparative Example 33, Step C (30.0 g, 104.5 mmol) in CH2Cl2 (500 mL) under nitrogen at -20° C. was added thionyl chloride (106.7 mL, 1,46 mmol). The resulting solution was stirred at room temperature overnight and then evaporated to dryness. The crude mixtue was diluted with toluene (50 mL), followed by the addition of more SOCl2 (106.7 mL) at room temperature. The resulting solution was heated to reflux for 2 hours until the reaction went to completion. The reaction mixture was then cooled to room temperature and concentrated to dryness to give a light brown solid (292) (35.67 g, 100percent yield, MBrCl=191). To a suspension of Mg (3.63 g) in anhydrous THF (95 mL) under nitrogen at room temperature was added 4-chloro-1-methyl piperidine (3 mL, 10percent of the total amount) and one small crystal of iodine. The resulting solution was heated to reflux, followed by the addition of iodomethane (0.5 mL) and the remainder of the 4-chloro-1-methyl piperidine (27 mL).

The reaction was stirred for one hour and then concentrated to dryness to give the crude Grignard reagent (0.8M). To a stirred solution of the chloro compound (292) from Preparative Example 34, Step A (35.67 g, 116.7 mmol) in anhydrous THF (200 mL) under nitrogen at room temperature, was added dropwise the Grignard reagent (as obtained above) (0.8M, 146 mL, 116.7 mmol).The resulting solution was stirred at room temperature for 3 hours, followed by the extraction with EtOAc-H2O. The combined organic layer was dried over MgSO4, filtered and evaporated to dryness to give the product (293) (49.25 g, 100percent yield, MH+=368).

To a stirred solution of Compound (293) from Step B above (42.9 g, 116.5 mmol) in toluene (400 mL) under nitrogen was added triethylamine (49 mL, 349.5 mmol). The resulting solution was heated to refux, followed by the dropwise addition of ethyl chloroformate (126 g, 1165 mmol). Continued to heat the solution at the reflux temperature for 2 hours. The reaction was then stirred at room temperature overnight, followed by extraction with an EtOAc-1N NaOH solution. The combined organic layer was dried over MgSO4, filtered, concentrated to dryness and the crude product purified by column chromatography on normal phase silica gel, eluding with 30percent EtOAc/70percent Hexane to give a light yellow solid (294) (2.99 g, 12percent yield, MH+=426.3).

A solution of the ester (294) from step C above (3.34 g, 7.83 mmol) in 6N HCl (20 mL) was heated to reflux overnight. The reaction was cooled to room temperature and basified with NH4OH solution, followed by extraction with CH2Cl2. The combined organic layer was dried over MgSO4, filtered, and evaporated to dryness to give a crude free piperidine (2.80 g, 100percent yield, MH+=534) To the crude material (as obtained above) (2.77 g, 7.82 mmol) in 50percent MeOH/1percent H2O (200 mL) was added Di-tert-butyl dicarbonate (3.41 g, 15.64 mmol). A

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106

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Duncia, John V.; Santella, Joseph B.; Wacker, Dean A.; Yao, Wenqing; Zheng, Changsheng

Patent: US2002/156102 A1, 2002 ;

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79.F:Part F.

Part F. Preparation of Carbamic Acid, [(1R)-3-[(3S)-3-[(4-fluorophenyl)methyl]-1-piperidinyl]-1-methyl-3-oxopropyl]-, 1,1-dimethylethyl Ester Butanoic acid, 3-[[(1,1-dimethylethoxy) carbonyl]amino]-, (3R)-(411 mg, 2.02 mmol, 1 equiv.), 4-fluorobenzyl)piperidine (obtained as the free base from XXX (391 mg, 2.02 mmol, 1 equiv.), and benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP reagent)(1.16 g, 2.22 mmol, 1.1 equiv.) were mixed in methylene chloride at 0° C. under N2 followed by the addition of triethylamine (0.56 ml, 4.04 mmol, 2 equiv.) which was added last. The contents were warmed to 25° C. After 16 hours the reaction was stripped then purified over silica gel in 1:1 hexanes/EtOAc. Obtained 750 mg of an amber oil as product. NMR (300 MHz, CDCl3) δ 7.20-7.00(m, 2H), 7.00 -6.80(m, 2H), 5.40-5.20 (m, 1H), 4.40 (m, 1H),4.00 -3.60 (m, 2H), 3.10-2.20 (m, 6H), 1.90-1.40 (m, 3H), 1.41 s, 9H) 1.50-1.30 (m, 2H), 1.30-1.00 (m, 3H). A

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107

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Bhyrappa, Puttaiah; Purushothaman, Bhavana

Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 2 p. 238 - 242 Title/Abstract Full Text View citing articles Show Details

in toluene

T=25°C; Equilibrium constant;

108

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Bhyrappa, Puttaiah; Purushothaman, Bhavana

Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 2 p. 238 - 242 Title/Abstract Full Text View citing articles Show Details

in toluene

T=25°C; Equilibrium constant;

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109

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Bhyrappa, Puttaiah; Purushothaman, Bhavana

Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 2 p. 238 - 242 Title/Abstract Full Text View citing articles Show Details

in toluene

T=25°C; Equilibrium constant;

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110

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With sulfuric acid in methanol; water

T=80 - 90°C; Kinetics; Further Variations:Temperatures;

Laudien, Robert; Mitzner, Rolf

Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 11 p. 2230 - 2232 Title/Abstract Full Text View citing articles Show Details

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111

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in benzene

T=25°C; Equilibrium constant;

Tayh, Jamal A.; Scott, Ronald M.

Journal of Molecular Structure, 1990 , vol. 237, # 1 p. 297 - 305 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

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112

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Rx-ID: 5314667 Find similar reactions

Nudelman, Norma S.; Garcia Linares, Guadalupe E.

Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1629 - 1635 Title/Abstract Full Text View citing articles Show Details

in tetrahydrofuran; benzene-d6

T=20°C; Addition; elimination; 0.25 h; Product distribution;

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113

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Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

114

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Rx-ID: 8632888 Find similar reactions

Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

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115

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Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

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116

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in acetonitrile

Magonski, Jozef; Rajzer, Barbara

T=24.84°C; complex dissociation; Equilibrium constant;

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

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117

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Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

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118

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Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

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119

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Magonski, Jozef; Rajzer, Barbara

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 6 p. 1181 - 1185 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=24.84°C; complex dissociation; Equilibrium constant;

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120

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With thiophene; hydrogen; aluminum oxide; P modified NiMo

T=280°C; P=15001.2 Torr; other Ni, Mo, P catalysts;

Damyanowa, Sonia; Spojakina, Alla; Vit, Zdenek

Collection of Czechoslovak Chemical Communications, 1992 , vol. 57, # 5 p. 1033 - 1042 Title/Abstract Full Text Show Details

With hydrogen; Ni-W sulfide

T=280°C; Catalytic hydrogenation; hydrodenitrogenation; P=15001.2 Torr; Kinetics; Further Variations:CatalystsTemperatures;

Gulkova, Daniela; Zdrazil, Miroslav

Collection of Czechoslovak Chemical Communications, 1999 , vol. 64, # 4 p. 735 - 746 Title/Abstract Full Text View citing articles Show Details

121

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With phosphate buffer; sodium perchlorate; sodium bromide in water

T=25°C; Rate constant;

Rx-ID: 5083556 Find similar reactions

Antelo, Juan M.; Arce, Florencio; Crugeiras, Juan; Gray, Edward T.; Yebra, Patricia

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 3 p. 651 - 655 Title/Abstract Full Text View citing articles Show Details

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122

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Crampton, Michael R.; Delaney, Jeannette; Rabbitt, Lynsey C.

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 11 p. 2473 - 2480 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; Elimination; Equilibrium constant;

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123

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With tetrahydropyridine hydrochloride in dimethyl sulfoxide

T=25°C; Elimination; Equilibrium constant;

Crampton, Michael R.; Delaney, Jeannette; Rabbitt, Lynsey C.

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 11 p. 2473 - 2480 Title/Abstract Full Text View citing articles Show Details

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124

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Zeneca Limited

Patent: US5889024 A1, 1999 ; Title/Abstract Full Text Show Details

17.f:Q1 =4-Methyl-4-(2-oxopiperidino)piperidino; MS: m/z=525(M+1).

f. 4-Methyl-4-(2-oxopiperidino)piperidine. Using the procedure of Example 1.o., replacing 1-benzyloxycarbonyl-4-(2-oxopiperidino)-4-(pyrrolidine-1-ylcarbonyl)piperidine with 1-benzyl-4-methyl-4-(2-oxopiperidino)piperidine, the piperidine was obtained as a white solid; MS: m/z=197(M+1); NMR (CD3 OD): 3.33 (m,2), 2.78 (m,4), 2.36 (m,4), 1.79 (m,6), 1.36 (s,3).

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Zeneca Limited

Patent: US5534525 A1, 1996 ; Title/Abstract Full Text Show Details

4.b.14.b.f:EXAMPLES 4.b.-14.b.

f. 4-Methyl-4-(2-oxopiperidino)piperidine. Using the procedure of Example 1.o., replacing 1-benzyloxycarbonyl-4-(2-oxopiperidino)-4-(pyrrolidin-1-ylcarbonyl) piperidine with 1-benzyl-4-methyl-4-(2oxopiperidino)piperidine, the piperidine was obtained as a white solid; MS: m/z=197(M+1); NMR (CD3 OD): 3.33 (m,2), 2.78 (m, 4), 2.36 (m,4), 1.79 (m,6), 1.36 (s,3).

125

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With sodium tetrahydroborate; nickel monoaluminide in tetrahydrofuran; ethanol; toluene

Merck and Co., Inc.

Patent: US5929243 A1, 1999 ;

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1.F:Step C

A mixture of piperidone 3 (349 mg, 1.34 mmol) Lawesson's reagent (594 mg, 1.47 mmol) and toluene (1.5 mL) was heated to 110° C. for 2 h. The mixture was cooled to 25° C., aged for 15 min, and filtered through a cotton plug, washing with toluene (3.5 mL). The filtrate was evaporated, and the residue containing thiolactam 4 was dissolved in THF (2 mL) and EtOH (2 mL). A 50percent aqueous slurry of Raney nickel (1 mL) was added. After a 5 min age another portion of the Raney nickel (1 mL) was added followed by NaBH4 (25 mg). After 15 min the mixture was filtered through a pad of solkafloc, washing the pad with THF (5 mL) and EtOH (5 mL). The filtrates were evaporated to 4 mL and diluted with MTBE (20 mL). The mixture was extracted with 0.5M aqueous HCl (2*3 mL), and the aqueous extract was basified with 5M aqueous NaOH (0.7 mL). The aqueous mixture was extracted with CH2 Cl2 (2*3 mL). The organic extracts were dried over Na2 SO4 and evaporated to give piperidine 5 (100 mg, 30percent) as a colorless oil: 13 C NMR (62.9 MHz, CDCl3) δ 175.1, 136.5, 129.6, 127.8, 126.4, 60.2, 53.1, 47.8, 46.1, 44.3, 32.8, 24.3, 13.9. HPLC analysis of the Marfey's derivative of 5 indicated >99.5 percent ee. A

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126

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With hydrogen; nickel oxynitride

T=210°C; P=759.811 Torr; further catalysts and temperatures; activity and selectivity of different catalysts; Product distribution; A

127

Elkamel; Elidrissi; Yacoubi; Nadiri; Abouarnadasse

Journal de Chimie Physique et de Physico-Chimie Biologique, 1998 , vol. 95, # 10 p. 2157 - 2179 Title/Abstract Full Text View citing articles Show Details

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Merck Sharp and Dohme, Ltd.

Patent: US5854268 A1, 1998 ;

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70.c:c

c 4-([N-(R)-α-Hydroxymethylbenzyl]aminomethyl)-4-hydroxy-1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)piperidine The title compound was prepared (290 mg, 68percent) from the foregoing piperidine and the mesylate prepared from 3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol in propan-2-ol using potassium carbonate as base, mp>55° C. MS, ES+, m/z=475 for (M+H)+. (Found: C, 66.73; H, 7.30; N, 16.87. C27 H34 N6 O2.0.8 H2 O requires C, 66.32; H, 7.34; N, 17.19percent. A

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128

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Sanofi

Patent: US5726313 A1, 1998 ;

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5.A:A

A 1-Benzoyl-3-(3,4-dichlorophenyl)-3-(tetrahydropyranyl-2-oxy)piperidine 0.4 ml of triethylamine is added, with stirring, to a solution of 900 mg of the piperidine obtained according to PREPARATION 2 in 10 ml of methylene chloride. A

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129

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Rx-ID: 4704126 Find similar reactions

Crampton, Michael R.; Lord, Simon D.

Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 2 p. 369 - 376 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=25°C; Equilibrium constant;

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130

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Crampton, Michael R.; Lord, Simon D.

Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 2 p. 369 - 376 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=25°C; Equilibrium constant;

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131

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Crampton, Michael R.; Lord, Simon D.

Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 2 p. 369 - 376 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

T=25°C; Equilibrium constant;

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132

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D: 83%

in acetonitrile

Ambient temperatureIrradiation; Rate constantProduct distributionMechanism;

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Gonzalez-Blanco, Roberto; Bourdelande, Jose L.; Marquet, Jordi

Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6903 - 6910 Title/Abstract Full Text View citing articles Show Details

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133

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With Pt on TiO2 in water

Irradiationdifferent Pt loading of catalyst; Rate constant;

Ohtani, Bunsho; Iwai, Kunihiro; Nishimoto, Sei-Ichi; Sato, Shinri

Journal of Physical Chemistry B, 1997 , vol. 101, # 17 p. 3349 - 3359 Title/Abstract Full Text View citing articles Show Details

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134

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Zeneca Limited

Patent: US5635509 A1, 1997 ;

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13.c:5-[(1RS,2SR)-1-Acetoxy-2-(3,4-dichlorophenyl)-4-(4-(1-ethyl-1-hydroxypropyl)piperidino)butyl]-1-phenylpyrazole Citrate Salt

c. 4-(1-Ethyl-1-hydroxypropyl)piperidine. A solution of 1-(benzyloxycarbonyl)-4-(1-ethyl-1-hydroxypropyl)piperidine (2.44 g) in ethanol (50 mL) was hydrogenated over 10percent palladium on carbon (100 mg, 3.45 bar) for 4 hours. The mixture was filtered and evaporated to afford the piperidine as a clear oil which solidified upon standing (1.37 g); NMR: 3.26 (broad d,2), 2.69 (m,2), 1.71 (broad d,2), 1.60-1.39 (m,7), 0.86 (t,6) A

135

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Zeneca Limited

Patent: US5654299 A1, 1997 ;

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7:N-[2-(3,4-Dichlorophenyl)-4-[4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

EXAMPLE 7 N-[2-(3,4-Dichlorophenyl)-4-[4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidino]butyl]-N-methylbenzamide hydrochloride Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine, the title compound was obtained as a white solid; mp 121°-124° C.; NMR: 7.61-7.19 (m, 8), 3.82-3.75 (m, 2), 3.07, 2.77 (2s, 3, N--CH3), 2.51 (s,3), 2.40-2.00 (broad m, 8); MS: m/z=529(M+1+28), m/z=501[(M+1), 35 Cl2 ].

Analysis for C26 H30 Cl2 N4 O2 *1.0 HCl*0.25 H2 O: Calculated: C, 57.57; H, 5.85; N, 10.33; Found: C, 57.53; H, 6.01; N, 10.06. The intermediate piperidine was prepared as follows. A

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136

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Zeneca Limited

Patent: US5654299 A1, 1997 ;

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7.e:e.

e. 4-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidine A solution of 1-benzyloxycarbonyl-4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine (0.18 g) in ethanol (5 mL) was hydrogenated over 10percent palladium on carbon (0.050 g) at a hydrogen pressure of 1 bar for 2 hours. The catalyst was then removed by filtration through diatomaceous earth, the filter cake was washed with ethanol and the solvent evaporated to afford the piperidine as a white crystalline solid (0.98 g); mp 64°-66° C.; NMR (CDCl3): 3.17 (m, 2), 2.98 (m, 1), 2.75 (dr,2, J=2.6, 12.0), 2.51 (s,3), 2.01 (m, 2), 1.75 (m, 2); MS: m/z=196(M+1+28). A

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Zeneca Limited

Patent: US5654299 A1, 1997 ;

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8:N-[2-(3,4-Dichlorophenyl)-4-[4-(4-ethoxycarbonylimidazol-2-yl)piperidino]butyl]-N-methylbenzamide

EXAMPLE 8 N-[2-(3,4-Dichlorophenyl)-4-[4-(4-ethoxycarbonylimidazol-2-yl)piperidino]butyl]-N-methylbenzamide Using a procedure similar to that described in Example 1 (alternative preparation), except using 4-(4-ethoxycarbonylimidazol-2-yl)piperidine, the title compound was obtained as a white solid; mp 96°-102° C.; NMR: 7.60-7.05 (m, 9), 4.30 (q,2, J=7.2), 3.78 (m, 2), 3.04, 2.77 (2s, 3, N--CH3), 2.20-1.75 (m, 8), 1.34 (t, 3, J=7.2); MS: m/z=585[(M+1+28), 35 Cl], m/z=559[(M+1), 37 Cl],

m/z=557[(M+1), 35 Cl]. Analysis for C29 H34 Cl2 N4 O3 *0.5 H2 O: Calculated: C, 61.48; H, 6.23; N, 9.89; Found: C, 61.69; H, 6.35; N, 9.59. The starting piperidine was prepared as follows. A

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138

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Amersham International plc

Patent: US5658494 A1, 1997 ;

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16:p-Styryldiphenylphosphine oxide (12)

p-Styryldiphenylphosphine oxide (12) Hydrogen peroxide (30percent w/v, 7 ml) was added dropwise to styryldiphenylphosphine (8.4 g, 29.2 mmole) in tetrahydrofuran (100 ml) at 5° C. over 30 minutes. The reaction mixture was then stirred at room temperature for 2 hours. The solvent was then evaporated and the product dried under vacuum at room temperature to give a clear oil (8.8 g). Preparation of Tetrakis(2,2,6,6-tetramethyl-3,5-heptanedionato)terbium(III)piperidine salt (13) 2,2,6,6-tetramethyl-3,5-heptanedione (0.92 g, 5 mmole) and piperidine (0.43 g, 5 mmole) were heated at 70° C. in ethanol (30 ml) for 20 minutes. A

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139

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Merck, Sharp and Dohme, Ltd.

Patent: US5686463 A1, 1997 ; Title/Abstract Full Text Show Details

32.c:c

c Cis N,N,Diethyl 4-Methoxycarbonyl-1-methoxycarbonylmethyl piperidine-3-carboxamide The foregoing crude pyridinium salt (36.0 g, 0.093 mol) was treated with Raney nickel in methanol (200 ml) to remove sulphur containing impurities and filtered. The filtrate was hydrogenated over platinum oxide (600 mg) at 50 psi and 50° until uptake ceased (72 h). The solution was filtered through Hyflo, evaporated and partioned between 2M potassium carbonate and dichloromethane. Chromatography of the residue from the organic layer on silica in 3percent methanol in dichloromethane gave the desired piperidine (9.0 g) as an oil. m/e (CI) 315 (M+H+); δ(CDCl3) 1.09 and 1.22 (each 3H, t, J7 Hz, 2*CH2 CH3); 1.92-2.01 (1H, m, 5-CH ax); 2.25-2.34 (1H, m, 5-CH eq); 2.60-2.66 (2H, m, 4-CH, 6-CH); 2.75 (1H, dd, J4 Hz, 11 Hz, 3-CH); 2.84-2.90 (1H, m, 6-CH); 2.99

(1H, dd, J8 Hz, 11 Hz, 2-CH ax); 3.16-3.21 (1H, m, 2-CH, eq); 3.28-3.43 (6H, m, 2*CH2 CH3, CH2 CO2) and 3.66 and 3.70 (each 3H, s, 2*OCH3. A

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140

B: 89%

Rx-ID: 25355181 Find similar reactions

F. HOFFMANN-LA ROCHE AG; AGOURON PHARMACEUTICALS, INC.

Patent: EP780386 A1, 1997 ;

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7.F:7F.

7F. Preparation of Ia where R 1 and R 2 when taken together with the Carbon to which they are attached represent N-BOC-Piperidine. R 3 and R 4 are Hydrogen, and R 5 is 4-(4-Chlorophenoxy)phenyl, from a Compound of Formula (10b) 7-(tert-Butoxycarbonyl)-2-oxa-7-azaspiro[3.5]nonan-1-one obtained in Example 5I above, was immediately dissolved in N,N-dimethylformamide (4 ml), slowly added to a solution containing the sodium salt of 4-(4-chlorophenoxy)thiophenol (generated by the addition of sodium hydride power (340 mg, 14.17 mmol) to a solution of 4-(4-chlorophenoxy)thiophenol (3.00 g, 12.7 mmol) in N,N-dimethylformamide (19 ml), at 0°C and stirred for 30 minutes) over a 10-15 minute period, and was stirred an additional 15 minutes. The resulting slurry was heated to 80°C, stirred for 5 minutes, tert-butanol (2 ml) added, and the mixture cooled to room temperature over 20 minutes. The majority of the N,N-dimethylformamide was removed in vacuo, the pH adjusted to 3.5 using 2M aqueous hydrochloric acid and extracted into ethyl acetate (4 x 150 ml). The combined organic layers were dried over magnesium sulfate, concentrated in vacuoand the residue chromatographed over silica gel, eluding with 1percent to 10percent methanol/methylene chloride, to afford the piperidine acid, 4-[4-(4-chlorophenoxy)phenylthiomethyl]-N-(tert-butoxycarbonyl)-piperidin-4-yl carboxylic acid as a pale yellow oil (5 g, 89percent). 1H-NMR (OH not observed; CDCl ) δ 1.37 (s, 9H), 1.55 (m , 2H), 2.10 (m , 2H), 3.05 (m , 2H), 3.06 (s, 2H), 3.72 (m , 2H), 6.81 (d, J= 8.8 Hz, 2H), 6.85 (d, J= 8.9 Hz, 2H), 7.21 (d, J= 8.9 Hz, 2H), 7.30 (d, J= 8.7 Hz, 4H). 3 c c c c A

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141

Synthesize Find similar Rx-ID: 4594856 Find similar reactions

Bernasconi, Claude F.; Wenzel, Philip J.

Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; var. DMSO/H2O ratios; Rate constant;

142

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Bernasconi, Claude F.; Wenzel, Philip J.

Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; var. DMSO/H2O ratios; Rate constant;

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143

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Bernasconi, Claude F.; Wenzel, Philip J.

Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; var. DMSO/H2O ratios; Rate constant;

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144

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in water; dimethyl sulfoxide

T=20°C; var. DMSO/H2O ratios; Rate constant;

Bernasconi, Claude F.; Wenzel, Philip J.

Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453 Title/Abstract Full Text View citing articles Show Details

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145

Synthesize Find similar Rx-ID: 4595468 Find similar reactions

Bernasconi, Claude F.; Wenzel, Philip J.

Journal of the American Chemical Society, 1996 , vol. 118, # 46 p. 11446 - 11453 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; var. DMSO/H2O ratios; Rate constant;

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146

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A: 4.0 % Chromat. B: 37 % Chromat. C: 2.0 % Chromat. D: 2.0 % Chromat. E: 20.0 % Chromat.

With ammonia; hydrogen; Katalco 58

T=230°C; P=26252.1 Torr; other heterogenous Cu-, Ni-, Co- and Fe-containing bifunctional catalyst systems; Product distribution;

Glebov; Kliger; Shuikin; Zaikin

Petroleum Chemistry, 1996 , vol. 36, # 4 p. 346 - 352 Title/Abstract Full Text View citing articles Show Details

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147

Synthesize Find similar Rx-ID: 4752052

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Hasegawa, Yoshinori; Sekiguchi, Shizen

Journal of Chemical Research, Miniprint, 1996 , # 5 p. 1201 - 1219 Title/Abstract Full Text Show Details

in dimethyl sulfoxide

T=25°C; Equilibrium constant;

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148

Synthesize Find similar Rx-ID: 4752073 Find similar reactions

Hasegawa, Yoshinori; Sekiguchi, Shizen

Journal of Chemical Research, Miniprint, 1996 , # 5 p. 1201 - 1219 Title/Abstract Full Text Show Details

in dimethyl sulfoxide

T=25°C; Equilibrium constant;

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149

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Hasegawa, Yoshinori; Sekiguchi, Shizen

Journal of Chemical Research, Miniprint, 1996 , # 5 p. 1201 - 1219 Title/Abstract Full Text Show Details

in dimethyl sulfoxide

T=25°C; Equilibrium constant;

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150

Rx-ID: 8211677 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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15.b:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-[3-(ethoxycarbonylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidino]butyl ]-H-methylbenzamide citrate.

b. 4-[3-(Ethoxycarbonylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-[3-(ethoxycarbonylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidine, the piperidine was obtained as a viscous oil; MS: m/z=270(M+1); NMR (CDCl3): 4.41 (m,1), 4.19 (q,2, J=7.1), 4.07 (s,2), 3.32 (m,2), 3.24 (m,2), 3.12 (m,2), 2.70 (m,2), 2.09 (m,1), 1.98 (m,2), 1.63 (m,4), 1.27 (t,3, J=7.1). A

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151

Rx-ID: 24519748 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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8.c:(S)-N-[2-(3,4-Dichlorophenyl)-4-[-4-(2-oxo-1,3-perhydrodiazepin-1-yl) piperidino]butyl]-N-methylbenzamide dihydrochloride.

c. 4-(2-oxo-1,3-perhydrodiazepin-1-yl)piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-(2-oxo-1,3-perhydrodiazepin-1-yl)piperidine, the piperidine was obtained as a white solid; MS: m/z=198(M+1); NMR (CD3 OD): 4.16 (m,1), 3.29 (m,2), 3.21 (m,2), 3.11 (m,2), 2.65 (m,2), 1.62 (m,6), 1.48 (m,2). A

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152

Rx-ID: 24519749 Find similar reactions

Zeneca Limited

Patent: US5589489 A1, 1996 ;

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67.b:EXAMPLE 67

b. 4-[R*)-2-Methysulfinylphenyl]piperidine. A solution of 1-benzyloxycarbonyl-4-[(R*)-2-methylsulfinylphenyl]piperidine (0.55 g) in trifluoroacetic acid (12 mL) was refluxed for 30 minutes. The reaction mixture was evaporated and the residue was triturated with ether. The resulting material was dried under reduced pressure to afford the piperidine as a hygroscopic solid (0.52 g); MS: m/z 224; NMR: 1.88 (m,2), 2.2 (s,3), 3.11 (m,3), 3.57 (s,2), 7.73 (m,4). A

153

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Rx-ID: 24519750 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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5.a:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-oxoperhydro-pyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide dihydrochloride.

a. 1-Benzyloxycarbonyl-4-(3-aminopropylamino)piperidine. Using the procedure of Example 3.a, replacing ethylenediamine with 1,3-diaminopropane, the piperidine was obtained as a viscous oil; MS: m/z=292(M+1); NMR (CD3 OD): 7.34 (m,5), 5.10 (s,2), 4.13 (m,2), 2.86 (m,2), 2.65 (m,5), 1.90 (m,2), 1.65 (m,2), 1.23 (m,2). A

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154

Rx-ID: 24519751 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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9.c:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-oxo-5,5-dimethyl-perhydropyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide.

c. 4-(2-Oxo-5,5-dimethylperhydropyrimidin-1-yl)piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-(2-oxo-5,5-dimethylperhydropyrimidin-1-yl)piperidine, the piperidine was obtained as a white solid; MS: m/z=212(M+1); NMR (CD3 OD): 4.28 (m,1), 3.10 (m,2), 2.92 (m,2), 2.89 (m,2), 2.66 (m,2), 1.59 (m,4), 1.03 (s,6). A

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155

Rx-ID: 24519752 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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10.c:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-methyl-2-oxoperhydropyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide citrate.

c. 4-(3-Methyl-2-oxoperhydropyrimidin-1-yl)piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-(3-methyl-2-oxoperhydropyrimidin-1-yl)piperidine, the piperidine was obtained as a viscous oil; MS: m/z=198(M+1); NMR (CD3 OD): 4.19 (m,1), 3.14 (m,4), 2.98 (m,2), 2.80 (s,3), 2.53 (m,2), 1.82 (m,2), 1.48 (m,4). A

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156

Rx-ID: 24519753 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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11.b:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(3-ethyl-2-oxoperhydro-pyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide citrate.

b. 4-(3-Ethyl-2-oxoperhydropyrimidin-1-yl)piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-(3-ethyl-2-oxoperhydropyrimidin-1-yl)piperidine, the piperidine was obtained as a viscous oil; MS: m/z=212(M+1); NMR (CDCl3): 4.45 (m,1), 3.38 (q,2, J=7.1), 3.17 (m,6), 2.72 (m,2), 2.15 (m,1), 1.91 (m,2), 1.62 (m,4), 1.10 (t,2, J=7.1). A

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157

Rx-ID: 24519754 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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13.b:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-[3-(N-methylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidino]butyl]-N-methylbenzamide citrate.

b. 4-[3-(N-Methylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]-piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-[3-(N-methylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidine, the piperidine was obtained as a gum; MS: m/z=255(M+1); NMR (CDCl3): 6.70 (m,1), 4.38 (m, 1), 3.92 (s,2), 3.35 (m,2), 3.23 (m,2), 3.14 (m,2), 2.81 (s,1.5), 2.79 (s,1.5), 2.72 (m,2), 2.10 (m,1), 1.97 (m,2), 1.64 (m,4). A

158

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Rx-ID: 24519755 Find similar reactions

Zeneca Limited

Patent: US5567700 A1, 1996 ;

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14.b:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-[3-(N-benzylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidino]butyl]-N-methylbenzamide citrate.

b. 4-[3-(N-Benzylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]-piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-[3 -(N-benzylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidine, the piperidine was obtained as a viscous oil; MS: m/z=331(M+1); NMR (CD3 OD): 7.29 (m,5), 4.39 (s,2), 4.30 (m,1), 4.00 (s,2), 3.30 (m,4), 3.16 (m,2), 2.73 (m,2), 1.98 (m,2), 1.68 (m,4). A

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159

B: 55%

Rx-ID: 24519756 Find similar reactions

Pfizer Inc.

Patent: US5538984 A1, 1996 ;

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5.b:b

b 6-Methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole The procedure described in Example 1e was followed using the piperidine formed in step a (0.49 g, 1.36 mmol) and TFA (7 mL) in CH2 Cl2 (7 mL), and triethylamine (0.85 mL, 6.1 mmol) and benzyl bromide (0.165 mL, 1.39 mmol) in CH2 Cl2 (8 mL). After purification, the title compound (0.265 g, 55percent) was obtained as a white solid. M.p. 90.5°-91.5° C. 1 H NMR (CDCl ) δ7.47 (d, J=8.7, 1H), 7.21-7.33 (m, 5H), 6.98 (d, J=1.8, 1H), 6.90 (dd, J =8.7, J =2.0, 1H), 3.88 (s, 3H), 3.50 (s, 2H), 2.88-2.98 (m, 4H), 1.96 (br t, J=10.6, 2H), 1.74-1.83 (m, 4H), 1.27-1.34 (m, 3H). 3 1 2 C NMR δ164.8, 162.0, 158.3, 138.4, 129.2, 128.1, 126.9, 121.4, 115.0, 113.8, 92.6, 63.4, 55.7, 53.7, 35.3, 34.3, 32.6, 22.6. IR (KBr) 2924, 2913, 2797, 2758, 1625, 1608, 1276, 1196, 1154, 734 cm-1. EIMS 349.2, 333.6, 259.1, 185.1, 172.1, 91.0 (base). Calc'd for C22 H26 N2 O2:C, 75.40; H, 7.48; N, 7.99. Found: C, 75.52; H, 7.63; N, 7.94. 13

160

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Zeneca Limited

Patent: US5567700 A1, 1996 ;

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12.c:(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-[3-(N,N-dimethyl-carbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidino]butyl]-N2-methylbenzamide citrate.

c. 4-[3-(N,N-Dimethylacetamido)-2-oxoperhydropyrimidin-1-yl]piperidine. Using the procedure of Example 1.j, replacing 1-benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine with 1-benzyloxycarbonyl-4-[3-(N,N-dimethylcarbamoylmethyl)-2-oxoperhydropyrimidin-1-yl]piperidine, the piperidine was obtained as a white solid by trituration from ether; MS: m/z=269(M+1); NMR (CDCl3): 4.40 (m,1), 4.12 (s,2), 3.35 (m,2), 3.24 (m,2), 3.11 (m,2), 3.02 (s,3), 2.95 (s,3), 2.69 (m,2), 2.14 (m, 1), 1.98 (m,2), 1.64 (m,4).

161

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Rx-ID: 24573493 Find similar reactions

48%

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With triethylamine in diethyl ether; dichloromethane; trifluoroacetic acid

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Pfizer Inc.

Patent: US5538984 A1, 1996 ; Title/Abstract Full Text Show Details

4.b:b

b 5-Methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole maleate The procedure described in Example 1e was followed using the piperidine formed in step a (0.58 g, 1.61 mmol) and TFA (7 mL) in CH2 Cl2 (7 mL), and triethylamine (0.50 mL, 3.6 mmol) and benzyl bromide (0.195 mL, 1.64 mmol) in CH2 Cl2 (10 mL). After purification, the title compound, free base (0.27 g, 48percent) was obtained as a clear oil. The maleate salt was prepared by adding a solution of maleic acid (0.080 g, 0.69 mmol) in Et2 O (10 mL) to a solution of the free base (0.24 g, 0.68 mmol) in Et2 O (20 mL).

With triethylamine in ethyl ether (Et2 O); methylene chloride (CH2 Cl2); diethyl ether; trifluoroacetic acid

Pfizer Inc.

Patent: US5538984 A1, 1996 ;

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2.b:b

b 5-Methyl-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole maleate The procedure described in Example 1e was followed using the piperidine formed in step a (0.910 g, 2.64 mmol) and TFA (13 mL) in methylene chloride (CH2 Cl2) (13 mL), and triethylamine (3.7 mL, 26.4 mmol) and benzyl bromide (0.32 mL, 2.69 mmol) in methylene chloride (CH2 Cl2) (20 mL). After purification, the title compound (free base) (0.56 g, 63percent) was obtained as a clear oil. The maleate salt was prepared by adding a solution of maleic acid (0.20 g, 1.72 mmol) in ethyl ether (Et2 O) (10 mL) to a solution of the free base (0.56 g, 1.67 mmol) in Et2 O (40 mL).

With triethylamine in CH2 Cl; diethyl ether; dichloromethane; trifluoroacetic acid

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Pfizer Inc.

Patent: US5538984 A1, 1996 ; Title/Abstract Full Text Show Details

3.b:b

b 5,6-Dimethyl-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole maleate The procedure described in Example 1e was followed using the piperidine formed in step a (1.04 g, 2.90 mmol) and TFA (16 mL) in CH2 Cl2 (16 mL), and triethylamine (4.2 mL, 29.0 mmol) and benzyl bromide (0.36 mL, 3.03 mmol) in CH2 Cl (20 mL). After purification, the title compound (free base) (0.53 g, 52percent) was obtained as a clear oil. The maleate salt was prepared by adding a solution of maleic acid (0.18 g, 1.55 mmol) in Et2 O (10 mL) to a solution of the free base (0.53 g, 1.52 mmol) in Et2 O (25 mL). Hide Details

With triethylamine in methylene chloride (CH2 Cl2); ethanol; dichloromethane; trifluoroacetic acid

Pfizer Inc.

Patent: US5538984 A1, 1996 ; Title/Abstract Full Text Show Details

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14.b:3-[2-[1-(Phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisothiazole maleate STR28 a) 4-[2-[1,2-Benzisothiazol-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl)ester.

b) 3-[2-[1-(Phenylmethyl)-4-piperidinyl]ethyl]-1, 2-benzisothaizole maleate The procedure described in Example 1e was followed using the piperidine formed in step a (0.102 g, 0.29 mmol) and trifluoroacetic acid (TFA) (0.75 mL) in methylene chloride (CH2 Cl2) (3 mL), and triethylamine (0.202 mL, 1.45 mmol) and benzyl bromide (0.038 mL, 0.32 mmol) in methylene chloride (CH2 Cl2) (3 mL). After purification, the title compound (free base) (0.058 g, 62percent) was obtained as a clear oil. The maleate salt was prepared by adding a solution of maleic acid (0.020 g, 0.17 mmol) in EtOH (3 mL) to a solution of the free base (0.058 g, 0.17 mmol) in CH2 Cl2 (3 mL). The resulting mixture was concentrated and the residue was triturated with Et2 O. The white solid obtained was filtered and collected to give the title compound (0.077 g, 96percent). 1 H-NMR (CDCl ) δ8.14-8.21 (m, 2H), 7.63 (t, J=7.4, 1H), 7.50-7.55 (m, 6H), 6.04 (s, 2H), 4.26 (br s, 2H), 3.35 (br s, 2H), 3.15 (t, J=7.6, 2H), 2.80-2.92 (m, 2H), 1.92-2.00 (m, 2H), 1.78-1.88 (m, 2H), 1.54-1.65 (m, 1H), 1.35-1.45 (m, 2H). 3 M.p.: 175°-176° C. C-NMR (DMSO-d6) δ167.3, 166.2, 151.6, 136.0, 134.2, 131.2, 130.1, 129.5, 128.9, 127.9, 124.9, 123.6, 120.6, 59.4, 51.6, 32.5, 33.5, 28.9, 27.8.

IR (KBr) 3030, 2910, 2350, 1700, 1575, 1445, 1350 cm-1. EIMS: 336.2 (M+, free base), 319.1, 245.1, 185.1, 172.1, 91.0 (base). Anal. Calcd. for C21 H24 N2 S.C4 H4 O4: C, 66.35; H, 6.24; N, 6.19. Found: C, 66.21; H, 5.93; N, 6.03.

162

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Rx-ID: 24573504 Find similar reactions

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With triethylamine in ethanol (EtOH); diethyl ether; dichloromethane; trifluoroacetic acid

Pfizer Inc.

Patent: US5538984 A1, 1996 ;

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6.b:b

b 7-Methoxy-3-[-2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole fumarate The procedure described in Example 1e was followed using the piperidine formed in step a (0.40 g, 1.11 mmol) and TFA (6 mL) in CH2 Cl2 (6 mL), and triethylamine (0.34 mL, 2.44 mmol) and benzyl bromide (0.14 mL, 1.18 mmol) in CH2 Cl2 (10 mL). After purification, the title compound (free base) (0.080 g, 21percent) was obtained as a clear oil. The fumarate salt was prepared by adding a solution of fumaric acid (0.025 g, 0.213 mmol) in ethanol (EtOH) (2 mL) to a solution of the free base (0.071 g, 0.203 mmol) in Et2 O (10 mL).

163

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Rx-ID: 24585226 Find similar reactions

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Adir Et Compagnie

Patent: US5508277 A1, 1996 ;

in tetrahydrofuran

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1:Example 1

The 9-allyl-2,6-dichloropurine used as starting material was prepared by reacting allyl alcohol and 2,6-dichloropurine in tetrahydrofuran according to the Mitsunobu method. The amine used as starting material was prepared by debenzylation of the corresponding piperidine melting at 78°-81° C., which was itself prepared by reductive alkylation with NaBH3 CN, in methanol, of a mixture of 1-benzylpiperidone and (10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methylamine hydrochloride melting (cap) at 275°-280° C. A

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164

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With p-TsOH; PtO2 in ethanol

The Dupont Merck Pharmaceutical Company

Patent: US5563158 A1, 1996 ;

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84.b:3-(Piperidin-4-yl)propan-1-ol p-toluenesulfonate:

EXAMPLE 84b 3-(Piperidin-4-yl)propan-1-ol p-toluenesulfonate: To a solution of 3-(4-pyridyl)propan-1-ol (15.13 g, 0.1103 mol) in EtOH (100 mL) was added p-TsOH (20.98 g, 0.1103 mol) and PtO2 (1.5 g, 6.6 mmol). The resulting mixture was placed on a Parr apparatus and hydrogenated at 55 p.s.i. After 6 hr, the mixture was filtered (EtOH wash) and the filtrate concentrated in vacuo, giving 36.78 g (>100percent) of the desired piperidine; 1 H NMR (300 MHz, CDCl3) δ 7.7 (d, 2H), 7.2 (d, 2H), 3.55 (t, 2H), 3.3 (m, 4H), 2.95 (bt, 2H), 2.38 (s, 3H), 1.95 (bd, 2H), 1.58 (m, 2H), 1.3 (m, 3H). A

165

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Rx-ID: 25412844 Find similar reactions

Zeneca Limited

Patent: US5534525 A1, 1996 ;

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Title/Abstract Full Text Show Details

4.b.14.b.c:EXAMPLES 4.b.-14.b.

c. 4-Methyl-4-(2-oxoperhydropyrimidin-1-yl)piperidine. Using the procedure of Example 1.o., replacing 1-benzyloxycarbonyl-4-(2-oxopiperidino)-4-(pyrrolidin-1-ylcarbonyl)piperidine with 1-benzyl-4-methyl-4-(2-oxoperhydroopyrimidin-1-ylcarbonyl) piperidine, the piperidine was obtained as a white solid; MS: m/z=198(M+1); NMR (CD3 OD): 3.26 (m,2), 3.17 (m,2), 2.77 (m,4), 2.44 (m,2), 1.89 (m,2), 1.67 (m,2), 1.31 (s,3). A

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166

Synthesize Find similar Rx-ID: 4102005 Find similar reactions

Cameron, James F.; Willson, C. Grant; Frechet, Jean M. J.

Journal of the Chemical Society, Chemical Communications, 1995 , # 9 p. 923 - 924 Title/Abstract Full Text View citing articles Show Details

in acetonitrile

2 h; Irradiation;

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167

Synthesize Find similar Rx-ID: 4419737 Find similar reactions

in water

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Bernasconi, Claude F.; Panda, Markandeswar; Stronach, Michael W.

T=25°C; Rate constant;

Journal of the American Chemical Society, 1995 , vol. 117, # 36 p. 9206 - 9212 Title/Abstract Full Text View citing articles Show Details

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168

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Rx-ID: 4419738 Find similar reactions

Bernasconi, Claude F.; Panda, Markandeswar; Stronach, Michael W.

Journal of the American Chemical Society, 1995 , vol. 117, # 36 p. 9206 - 9212 Title/Abstract Full Text View citing articles Show Details

in water

T=25°C; Rate constant;

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169

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Rx-ID: 4419739 Find similar reactions

Bernasconi, Claude F.; Panda, Markandeswar; Stronach, Michael W.

Journal of the American Chemical Society, 1995 , vol. 117, # 36 p. 9206 - 9212 Title/Abstract Full Text View citing articles Show Details

in water

T=25°C; Rate constant;

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170

Synthesize Find similar Rx-ID: 4448428 Find similar reactions

Um, Ik-Hwan; Kwon, Hye-Jin; Kwon, Dong-Sook

Journal of Chemical Research, Miniprint, 1995 , # 8 p. 1801 - 1817 Title/Abstract Full Text Show Details

in water; dimethyl sulfoxide

T=25°C; Rate constant;

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171

Synthesize Find similar Rx-ID: 5727254 Find similar reactions

With hydrogen sulfide; hydrogen; aluminum oxide; presulfidated Mo

T=319.9°C; flow microreactor; other catalysts; Rate constant;

Jian, M.; Cerda, J. L. Rico; Prins, R.

Bulletin des Societes Chimiques Belges, 1995 , vol. 104, # 4-5 p. 225 - 230 Title/Abstract Full Text Show Details

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172

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Rx-ID: 1783877 Find similar reactions

Chamberlin, Rachel A.; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994 , # 3 p. 425 - 432 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; var. conc. of reagents; Equilibrium constant;

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173

Synthesize Find similar Rx-ID: 1783878 Find similar reactions

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Chamberlin, Rachel A.; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994 , # 3 p. 425 - 432 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; var. conc. of reagents; Equilibrium constant;

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174

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Rx-ID: 1783879 Find similar reactions

Chamberlin, Rachel A.; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994 , # 3 p. 425 - 432 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; var. conc. of reagents; Equilibrium constant;

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175

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Rx-ID: 1783880 Find similar reactions

Chamberlin, Rachel A.; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994 , # 3 p. 425 - 432 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; var. conc. of reagents; Equilibrium constant;

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176

Rx-ID: 24454000 Find similar reactions

Merck Sharp and Dohme Limited

Patent: US5298520 A1, 1994 ;

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24:2.

To a solution of ammonium formate (0.32 g, 5.07 mmol) and 4-[5-(2-methylimidazol-1-yl)-1H-indol-3-yl]-N-benzylpiperidine (0.4 g, 1.08 mmol), in methanol (40 ml) was added Pd/C (10percent; 0.4 g) and the mixture stirred at 60° C. for 3h. The catalyst was removed by filtration through celite and the solvent removed under vacuum. The residue was taken up into H2 O (30 ml), basified with NH3 solution and extracted with ethyl acetate (3*100 ml). The combined extracts were dried (Na2 SO4) and evaporated and the residue chromatographed through silica-gel eluding with CH2 Cl2 /MeOH/NH3 (30:8:1) to give the desired piperidine (0.2 g). The bisoxalate dihydrate salt was prepared, mp 80° C. (hygroscopic); (Found: C, 50.53; H, 5.54; N, 10.87. C17 H20 N4.2(C2 H2 O4).2.2H2 O requires C, 50.43; H, 5.72; N, 11.20percent); 1 H NMR (360 MHz, D2 O) δ 1.91-2.03 (2H, m, CH2); 2.30-2.34 (2H, m, CH2); 2.55 (3H, s, CH3); 3.19-3.36 (3H, m, CH and CH2); 3.55-3.62 (2H, m, CH2); 7.28 (1H, dd, J=1.2 and 8.6 Hz, Ar-H); 7.44 (1H, s, Ar-H); 7.47 (1H, d, J=2.0 Hz, Ar-H); 7.52 (1H, d, J=2.0 Hz, Ar-H); 7.69 (1H, d, J=8.6 Hz, Ar-H); 7.82 (1H, d, J=1.2 Hz, Ar-H).

177

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Rx-ID: 32495 Find similar reactions

92%

With samarium diiodide in tetrahydrofuran; water

0.383333 h; Ambient temperature;

Kamochi, Yasuko; Kudo, Tadahiro

Heterocycles, 1993 , vol. 36, # 10 p. 2383 - 2396 Title/Abstract Full Text View citing articles Show Details

With ethanol; sodium

Fischer,O.

Chemische Berichte, 1899 , vol. 32, p. 1300 Full Text Show Details

178

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179

With hydrogen; platinum(IV) oxide in acetic acid

heat of hydrogenation; Thermodynamic data;

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Rx-ID: 1454240 Find similar reactions

Wiberg, Kenneth B.; Nakaji, David Y.; Morgan, Kathleen M.

Journal of the American Chemical Society, 1993 , vol. 115, # 9 p. 3527 - 3532 Title/Abstract Full Text View citing articles Show Details

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90%

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With samarium diiodide in tetrahydrofuran; water

0.633333 h; Ambient temperature;

Rx-ID: 1527174 Find similar reactions

Kamochi, Yasuko; Kudo, Tadahiro

Heterocycles, 1993 , vol. 36, # 10 p. 2383 - 2396 Title/Abstract Full Text View citing articles Show Details

180

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98%

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With samarium diiodide in tetrahydrofuran; water

0.3 h; Ambient temperature;

Rx-ID: 1532443 Find similar reactions

Kamochi, Yasuko; Kudo, Tadahiro

Heterocycles, 1993 , vol. 36, # 10 p. 2383 - 2396 Title/Abstract Full Text View citing articles Show Details

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181

Synthesize Find similar Rx-ID: 1783875 Find similar reactions

in dimethyl sulfoxide

T=25°C; Equilibrium constant;

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Chamberlin, Rachel; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993 , # 1 p. 75 - 82 Title/Abstract Full Text View citing articles Show Details

182

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Rx-ID: 1783876 Find similar reactions

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Chamberlin, Rachel; Crampton, Michael R.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993 , # 1 p. 75 - 82 Title/Abstract Full Text View citing articles Show Details

in dimethyl sulfoxide

T=25°C; Rate constant;

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183

Synthesize Find similar Rx-ID: 3541966 Find similar reactions

Forlani, Luciano

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993 , # 8 p. 1525 - 1530 Title/Abstract Full Text View citing articles Show Details

in cyclohexane

T=21°C; Equilibrium constant;

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184

Synthesize Find similar Rx-ID: 3542482 Find similar reactions

in cyclohexane

T=21°C; Equilibrium constant;

Forlani, Luciano

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993 , # 8 p. 1525 - 1530 Title/Abstract Full Text View citing articles Show Details

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185

Rx-ID: 24366392 Find similar reactions

Merck and Co., Inc.

Patent: US5206240 A1, 1993 ;

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3,4-Dihydro-6-methanesulfonamido-4-(hydroxyimino)-1'-(2-phenylethyl)-spiro[(2H)-1benzopyran-2,4'-piperidine]

3,4-Dihydro-6-methanesulfonamido-4-(hydroxyimino)-1'-(2-phenylethyl)-spiro[(2H)-1benzopyran-2,4'-piperidine] In the manner of Example 427, 3,4-dihydro-6-methane-sulfonamido-1'-(2-phenylethyl)-spiro [(2H)-benzopyran-2,4'-piperidine]-4-one was treated with hydroxylamine hydrochloride to give, after chromatography, the piperidine as a solid, m.p. 95°-99° C. Anal. Calc'd for C22 H27 N3 O4 S.0.6CHCl3: C, 54.16; H, 5.55; N, 8.39. Found: C, 54.37; H, 5.49; N, 8.48. A

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186

A: 93%

Hide Experimental Procedure

Rx-ID: 24366393 Find similar reactions

Merck and Co., Inc.

Patent: US5206240 A1, 1993 ; Title/Abstract Full Text Show Details

1'-Benzoyl-3,4-dihydro6-methanesulfonamido-spiro [(2H)-1-benzopyran-2,4'-piperidine]

1'-Benzoyl-3,4-dihydro6-methanesulfonamido-spiro [(2H)-1-benzopyran-2,4'-piperidine] Sodium borohydride (1.13 g, 30 mmol) was added in portions over 5 minutes to a stirred, ice cooled suspension of 1'-benzoyl-3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (prepared as described in Example 70, Method 2, Step C) (6.21 g, 15 mmol) in ethanol (150 ml). The mixture was stirred at room temperature for 22 hours, poured into water (150 ml) and the ethanol was evaporated under reduced pressure. The mixture was extracted with dichloromethane (4*150 ml) and the combined organic fractions were dried (Na2 SO4) and evaporated under reduced pressure to give a white foam (6.61 g). A sample (6.41 g) and p-toluenesulfonic acid (Monohydrate, 100 mg) in toluene (150 ml) were heated under reflux for 1 hr, cooled and diluted with methylene chloride (600 ml). The mixture was washed with aqueous sodium hydrogen carbonate (saturated, 150 ml), dried (Na2 SO4) and evaporated under reduced pressure. The residue was suspended in ethanol-methanol (1:1, 200 ml), palladium on carbon (5percent, 1 g) was added and the mixture was stirred under hydrogen (1 Atm.) for 24 hours. The mixture was filtered through celite, washing with methanol, and the filtrate was evaporated under reduced pressure. The residue was redissolved in dichloromethane, filtered through celite and evaporated under reduced pressure to give the piperidine as a foam (5.44 g, 93percent). 1 H NMR (CDCl ): δ7.4 (5H, s), 6.98 (2H, m), 6.83 (1H, d, J 8.4 Hz), 4.5 (1H, br m), 3.6-3.2 (3H, m), 2.96 (3H, s), 2.8 (2H, m), and 2.0-1.5 (7H, m). 3

187

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Rx-ID: 1498955 Find similar reactions

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Dannan; Crooks; Dittert; Hussain

Journal of Pharmaceutical Sciences, 1992 , vol. 81, # 7 p. 652 - 656 Title/Abstract Full Text View citing articles Show Details

in water

Rate constant;

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188

Synthesize Find similar Rx-ID: 1555527 Find similar reactions

With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10phenanthrolinedisulfonate); water

T=25°C; 24 h; pH 8; Rate constant;

Wang, Fengjiang; Sayre, Lawrence M.

Journal of the American Chemical Society, 1992 , vol. 114, # 1 p. 248 - 255 Title/Abstract Full Text View citing articles Show Details

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189

Synthesize Find similar Rx-ID: 1783873 Find similar reactions

in water; dimethyl sulfoxide

T=25°C; Rate constant;

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Terrier, Francois; Xiao, Lan; Farrell, Patrick G.; Moskowitz, Danielle

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1992 , # 8 p. 1259 - 1263 Title/Abstract Full Text View citing articles Show Details

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190

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Rx-ID: 1783874 Find similar reactions

Terrier, Francois; Xiao, Lan; Farrell, Patrick G.; Moskowitz, Danielle

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1992 , # 8 p. 1259 - 1263 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=25°C; Rate constant;

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191

Synthesize Find similar Rx-ID: 1920664 Find similar reactions

Smith, John R. Lindsay; Smart, Alison U.; Twigg, Martyn V.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1992 , # 6 p. 939 - 947 Title/Abstract Full Text Show Details

in water

T=300°C; 15 h; Rate constant;

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192

Synthesize Find similar Rx-ID: 2807433 Find similar reactions

With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10phenanthrolinedisulfonate); water

T=25°C; 24 h; pH 8; var. pH's; Rate constantProduct distribution;

Wang, Fengjiang; Sayre, Lawrence M.

Journal of the American Chemical Society, 1992 , vol. 114, # 1 p. 248 - 255 Title/Abstract Full Text View citing articles Show Details

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193

Synthesize Find similar Rx-ID: 2807436 Find similar reactions

Wang, Fengjiang; Sayre, Lawrence M.

Journal of the American Chemical Society, 1992 , vol. 114, # 1 p. 248 - 255 Title/Abstract Full Text View citing articles Show Details

With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10phenanthrolinedisulfonate); water

T=25°C; 24 h; pH 8; var. pH's; Rate constantProduct distribution; A

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194

Synthesize Find similar Rx-ID: 3072192 Find similar reactions

Bernasconi, Claude F.; Zitomer, Janie L.; Schuck, David F.

Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1132 - 1139 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; Equilibrium constant;

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195

Synthesize Find similar Rx-ID: 3073216 Find similar reactions

in water; dimethyl sulfoxide

T=20°C; Equilibrium constant;

Bernasconi, Claude F.; Zitomer, Janie L.; Schuck, David F.

Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1132 - 1139 Title/Abstract Full Text View citing articles Show Details

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196

Synthesize Find similar Rx-ID: 3073229 Find similar reactions

Bernasconi, Claude F.; Zitomer, Janie L.; Schuck, David F.

Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1132 - 1139 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; Equilibrium constant;

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197

Synthesize Find similar Rx-ID: 3073859 Find similar reactions

Bernasconi, Claude F.; Zitomer, Janie L.; Schuck, David F.

Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1132 - 1139 Title/Abstract Full Text View citing articles Show Details

in water; dimethyl sulfoxide

T=20°C; Equilibrium constant;

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198

Synthesize Find similar Rx-ID: 3074108 Find similar reactions

in water; dimethyl sulfoxide

T=20°C; Equilibrium constant;

Bernasconi, Claude F.; Zitomer, Janie L.; Schuck, David F.

Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1132 - 1139 Title/Abstract Full Text View citing articles Show Details