Rac-1-benzyl-4-(2-nitro-1-phenyl-ethyl)-piperidine-4-carboxylic acid ethyl ester → Rac-4-(2-amino-1-phenyl-ethyl)-1-benzyl-piperidine-4-carboxylic acid ethyl ester

HRID 347302Notes

Reaction equation

HRID 347302 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][N+:21]([O-])=O)[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCO.[Ni]>[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][NH2:21])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66918187Rac-1-benzyl-4-(2-nitro-1-phenyl-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 66918079Rac-4-(2-amino-1-phenyl-ethyl)-1-benzyl-piperidine-4-carboxylic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of rac-1-benzyl-4-(2-nitro-1-phenyl-ethyl)-piperidine-4-carboxylic acid ethyl ester (3.18 g, 8 mmol) in dry EtOH (240 mL) was hydrogenated in the presence of Ra—Ni (3 g) at 60 bar at 55° C. for 3 h. After cooling and decompression of the reaction vessel, the mixture was filtered over celite and the filtrate evaporated to leave the title compound (2.9 g, 99%) as a clear oil. MS: m/e=367.4 (M+H).

Workup

  1. temperatureAfter cooling
  2. filtrationdecompression of the reaction vessel, the mixture was filtered over celite
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-0684659ad778449ba14920c174db2ac2
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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