Reaxys
PubChem
eMolecules
Reactions (20)
Yield
Substances (4)
Citations (10)
Conditions
References
1
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Rx-ID: 61805 Find similar reactions
With water
T=180°C; beim Erhitzen des Reaktionsprodukts mit wss. Schwefelsaeure <50prozentig>;
2
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Smith, Kline and French Labor.
Patent: US2454746 , 1947 ; Full Text Show Details
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Synthesize Find similar With acetic acid; platinum
Hydrogenation;
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Rx-ID: 332850 Find similar reactions
Zenitz; Macks; Moore
Journal of the American Chemical Society, 1947 , vol. 69, p. 1117,1120 Full Text Show Details
3
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Hydrogenation;
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Rx-ID: 412655 Find similar reactions
Zenitz; Macks; Moore
Journal of the American Chemical Society, 1947 , vol. 69, p. 1117,1120 Full Text Show Details
4
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Rx-ID: 435205 Find similar reactions
Smith, Kline and French Labor.
Patent: US2454746 , 1947 ; Full Text Show Details
5
Synthesize Find similar With L-(+)-tartaric acid
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Rx-ID: 435206 Find similar reactions
Smith, Kline and French Labor.
Patent: US2454746 , 1947 ; Full Text Show Details
6
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With acetic acid; platinum
Hydrogenation;
Rx-ID: 437203 Find similar reactions
Zenitz; Macks; Moore
Journal of the American Chemical Society, 1947 , vol. 69, p. 1117,1120 Full Text Show Details
7
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With lithium aluminium tetrahydride
Rx-ID: 455068 Find similar reactions
Blicke; Johnson
Journal of the American Pharmaceutical Association (1912-1977), 1956 , vol. 45, p. 443 Full Text View citing articles Show Details
8
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Rx-ID: 6188516 Find similar reactions
(+-)-PhCH2CH(CH3)NHCH3 (III) u. H2 an RuO2;
Abbott Labs.
Patent: US3014966 , 1961 ; Chem.Abstr., 1962 , vol. 56, # 12772b Full Text Show Details
(+-)-PhCH2CH(CH3)NHCH3 (III) u. H2 an Ru/Al2O3;
Abbott Labs.
Patent: US3014966 , 1961 ; Chem.Abstr., 1962 , vol. 56, # 12772b Full Text Show Details
Methyl-<2-chlor-1-methyl-2-phenyl-aethyl>-amin*HCl, MeOH, H2 <Pt>;
Dr.C. Freese
Patent: DE970480 , 1951 ; Chem.Abstr., 1960 , # 7590 Full Text Show Details
Cyclohexylaceton, wss. Methylamin, aktiv. Al, sd. EtOH;
Dr.C. Freese
Patent: DE970480 , 1951 ; Chem.Abstr., 1960 , # 7590 Full Text Show Details
9
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Rx-ID: 8933346 Find similar reactions
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Stage #1: With titanium(IV) isopropylate; triethylamine in ethanol
3 h; Stage #2: With sodium tetrahydroborate in ethanol
3 h; Further stages.;
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Fotsch; Sonnenberg; Chen; Hale; Karbon; Norman
Journal of Medicinal Chemistry, 2001 , vol. 44, # 14 p. 2344 - 2356 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 10526864 Find similar reactions
Stage #1: acetaldehyde; methylamine Stage #2: 1-chloromethylcyclohexane Grignard reaction;
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Nakahara, Yuji; Hanajiri, Ruri
Life Sciences, 2000 , vol. 66, # 7 p. 563 - 574 Title/Abstract Full Text View citing articles Show Details
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11
Synthesize Find similar Multi-step reaction with 2 steps 1: water / 180 °C / beim Erhitzen des Reaktionsprodukts mit wss. Schwefelsaeure <50prozentig> 2: Lg-tartaric acid View Scheme
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Rx-ID: 22031657 Find similar reactions
Smith, Kline and French Labor.
Patent: US2454746 , 1947 ; Full Text Show Details
12
Synthesize Find similar Multi-step reaction with 2 steps 1: water / 180 °C / beim Erhitzen des Reaktionsprodukts mit wss. Schwefelsaeure <50prozentig> 2: Lg-tartaric acid View Scheme
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Rx-ID: 22031658 Find similar reactions
Smith, Kline and French Labor.
Patent: US2454746 , 1947 ; Full Text Show Details
13
Synthesize Find similar Multi-step reaction with 2 steps 1: formic acid 2: LiAlH4
View Scheme
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Rx-ID: 22031660 Find similar reactions
Blicke; Johnson
Journal of the American Pharmaceutical Association (1912-1977), 1956 , vol. 45, p. 443 Full Text View citing articles Show Details
14
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With sodium hydroxide in water; toluene
Hide Experimental Procedure
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Rx-ID: 23854511 Find similar reactions
MALLINCKRODT INC.
Patent: WO2006/73547 A1, 2006 ; Location in patent: Page/Page column 8 ; Title/Abstract Full Text Show Details
3:
EXAMPLE 3.; )032] To a 100 ml 3-neck flask fitted with a mechanical stirrer, a condenser, a thermocouple, and a nitrogen purge stream was added 1.9468 g (0.01254 mole) of propylhexedrine, 2.65 g toluene, and 0.79 g (0.00624 mole) of benzyl chloride. The reactor was continuously purged with nitrogen. The reaction mass was heated to 1210C for 4.75 hr. A slurry of a crystalline solid in an oil formed. To this was added 4.60 g of toluene and 7.32 g of water. The mixture was vigorously stirred and heated to 5O0C for 10 minutes. The solids completely dissolved. After cooling, the two liquid phases were transferred to a separatory funnel. Water, (0.85 g) and a 1.62 g amount of toluene were used to rinse the residues in the flask into the separatory funnel. The layers were separated into a 9.10 g lower water layer containing the propylhexedrine hydrochloride and an 8.19 g upper organic layer containing the N-benzylpropylhexedrine. HPLC analysis of the organic layer found 20.76percent, by weight, of benzylpropylhexedrine base which is 1.70 g (0.00692 mole) which is a 110percent yield. The propylhexedrine hydrochloride in the water layer was converted to the base by adding 5.68 g of toluene and 1.18 g of 25percent sodium hydroxide. The mixture was aggressively shaken. The layers were separated into a 9.05 g water layer having a pH of 13 and a 6.79 g toluene layer. The toluene layer was analyzed by gas chromatography and found to contain 13.10percent, by weight, propylhexedrine base which is equivalent to 0.8895 g (0.00572 mole) or a 91.3percent yield.
15
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With 5 palladium on charcoal; hydrogen
T=55°C; P=3878.71 - 4137.29 Torr; 6 h;
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Rx-ID: 37769138 Find similar reactions
Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.
Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details
16
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Rx-ID: 37769143 Find similar reactions
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate / water / 12 h / 20 °C 2: Raney Ni / isopropyl alcohol / 50 - 55 °C / |Autoclave 3: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale 4: 5 palladium on charcoal; hydrogen / 6 h / 55 °C / 3878.71 4137.29 Torr View Scheme
Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.
Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details
17
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Multi-step reaction with 3 steps 1: Raney Ni / isopropyl alcohol / 50 - 55 °C / |Autoclave 2: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale 3: 5 palladium on charcoal; hydrogen / 6 h / 55 °C / 3878.71 4137.29 Torr View Scheme
Rx-ID: 37769149 Find similar reactions
Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.
Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details
18
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Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale 2: 5 palladium on charcoal; hydrogen / 6 h / 55 °C / 3878.71 4137.29 Torr View Scheme
Rx-ID: 37769155 Find similar reactions
Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.
Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details
A
B
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19
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Rx-ID: 3268802 Find similar reactions
With hydrogenchloride
Heating; Rate constant;
Rucker; Mrongovius; Neugebauer
Archiv der Pharmazie, 1982 , vol. 315, # 10 p. 839 - 846 Title/Abstract Full Text View citing articles Show Details
A
B
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20
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Rx-ID: 23831714 Find similar reactions
in water; toluene
T=50 - 121°C; 4.91667 h; Hide Experimental Procedure
MALLINCKRODT INC.
Patent: WO2006/73547 A1, 2006 ; Location in patent: Page/Page column 8 ; Title/Abstract Full Text Show Details
3:
EXAMPLE 3.; )032] To a 100 ml 3-neck flask fitted with a mechanical stirrer, a condenser, a thermocouple, and a nitrogen purge stream was added 1.9468 g (0.01254 mole) of propylhexedrine, 2.65 g toluene, and 0.79 g (0.00624 mole) of benzyl chloride. The reactor was continuously purged with nitrogen. The reaction mass was heated to 1210C for 4.75 hr. A slurry of a crystalline solid in an oil formed. To this was added 4.60 g of toluene and 7.32 g of water. The mixture was vigorously stirred and heated to 5O0C for 10 minutes. The solids completely dissolved. After cooling, the two liquid phases were transferred to a separatory funnel. Water, (0.85 g) and a 1.62 g amount of toluene were used to rinse the residues in the flask into the separatory funnel. The layers were separated into a 9.10 g lower water layer containing the propylhexedrine hydrochloride and an 8.19 g upper organic layer containing the N-benzylpropylhexedrine. HPLC analysis of the organic layer found 20.76percent, by weight, of benzylpropylhexedrine base which is 1.70 g (0.00692 mole) which is a 110percent yield. The propylhexedrine hydrochloride in the water layer was converted to the base by adding 5.68 g of toluene and 1.18 g of 25percent sodium hydroxide. The mixture was aggressively shaken. The layers were separated into a 9.05 g water layer having a pH of 13 and a 6.79 g toluene layer. The toluene layer was analyzed by gas chromatography and found to contain 13.10percent, by weight, propylhexedrine base which is equivalent to 0.8895 g (0.00572 mole) or a 91.3percent yield.