Ammonium Chloride → 4-Aminomethyl-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide

HRID 220980Notes

Reaction equation

HRID 220980 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([CH3:20])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2].[BH4-].[Na+].[NH4+].[Cl-]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([CH3:20])[C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[O:8])=[CH:5][C:4]=1[CH3:23]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 575552024-Cyano-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide

Product 1

HCID 575553064-Aminomethyl-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamideYield 79%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-cyano-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide from Example E118.2 (1.08 g, 3.4 mmol) in methanol (40 ml) at room temperature was treated with cobalt(II) chloride hexahydrate (1.61 g, 6.8 mmol). The mixture was stirred for 10 min then sodium borohydride (1.28 g, 34 mmol) was added portionwise. The mixture was stirred for 20 h then saturated NH4Cl solution (10 ml) was added. The mixture was stirred for 30 min, filtered through glass-fibre paper and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane) to yield the title compound (863 mg, 79%).

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred for 20 h
  3. stirringThe mixture was stirred for 30 min
  4. filtrationfiltered through glass-fibre paper
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane)

Sources & evidence

ORD record
ord-3c6e5c7524c64b10aa67ea5891e7a048
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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