4-(2-Cyano-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester → 4-(2-Aminomethyl-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1667539Notes

Reaction equation

HRID 1667539 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[C:22]#[N:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>N.CCO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[CH2:22][NH2:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 674174064-(2-Cyano-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 674174384-(2-Aminomethyl-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 94.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution of 4-(2-cyano-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (680 mg, 2.14 mmol) in NH3/EtOH (2M, 15 mL) was added Raney Nickel (5 mL slurry in water). The atmosphere was exchanged with hydrogen via balloon and the mixture was allowed to stir for 2.5 h. After this time the mixture was filtered through celite and concentrated to yield the title compound (650 mg). m/z (M+1) 321.57.

Workup

  1. filtrationAfter this time the mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a390b94b8a5a47ccb65a4b0a28887989
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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