Tert-butyl 4-[2-cyano-4-(trifluoromethyl)phenyl]piperazine-1-carboxylate → 4-(2-Aminomethyl-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1667537Notes

Reaction equation

HRID 1667537 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]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[C:24]#[N:25])[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]([C:20]([F:21])([F:22])[F:23])=[CH:16][C:15]=2[CH2:24][NH2:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59793685Tert-butyl 4-[2-cyano-4-(trifluoromethyl)phenyl]piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 674164364-(2-Aminomethyl-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 98.1%

Reagents, catalysts & solvents 2

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

Procedure

To a solution 4-(2-cyano-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (150 mg, 0.42 mmol) in NH3/EtOH (2M, 10 mL) was added Raney Nickel (3 mL slurry in water). The atmosphere was exchanged with hydrogen via balloon and the mixture was allowed to stir for 30 min. After this time the mixture was filtered through celite and concentrated to yield the title compound (148 mg). m/z (M+1) 360.23.

Workup

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

Sources & evidence

ORD record
ord-aa41e98393b74a2f86512878b1c764cc
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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