Ammonium Hydroxide → 4-(2-Aminomethyl-phenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amide

HRID 907569Notes

Reaction equation

HRID 907569 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]#[N:29])[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH4+].[OH-]>C(O)C.[Ni].O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([NH:13][C:14]([N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:28][NH2:29])[CH2:20][CH2:21]2)=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 37992314-(2-Cyanophenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide

Product 1

HCID 590139384-(2-Aminomethyl-phenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amideYield 105.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-(2-Cyanophenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (˜5.3 mmol) was dissolved in 50 mL of ethanol. 5 mL of aqueous NH4OH was added along with 500 mg of 50% Raney nickel in water. The reaction mixture was hydrogenated in a Parr shaker at 45 psi overnight. The reaction mixture was filtered through a plug of Celite and concentrated under vacuum. 2.5 g of crude product was obtained, and used without further purification.

Workup

  1. customwas hydrogenated in a Parr shaker at 45 psi overnight
  2. filtrationThe reaction mixture was filtered through a plug of Celite
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a654bc4f8b7344e194daf485aba0be0e
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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