Ammonium Hydroxide → Phenethylamine, m-trifluoromethyl-

HRID 638226Notes

Reaction equation

HRID 638226 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[NH4+]>[Ni].C(O)C>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 75360m-Trifluoromethylphenylacetonitrile

Product 1

HCID 104223Phenethylamine, m-trifluoromethyl-Yield 93.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7.20 g (38.9 mmole) 2-(3-trifluoromethylphenyl)acetonitrile, 0.75 g Raney Nickel, 30 ml ethanol and 4.0 ml concentrated ammonium hydroxide was flushed with nitrogen, then hydrogenated at 3.5 kg/cm2 for 18 hours. The catalyst was removed by filtration under nitrogen and the filtrate evaporated in vacuo to afford 6.86 g (93%) of the title amine as a red oil. 1H-NMR(CDCl3)ppm(delta): 0.65-1.40 (bs, 2H), 2.65-3.40 (m, 4H), 7.30-7.60 (m, 4H).

Workup

  1. customwas flushed with nitrogen
  2. customThe catalyst was removed by filtration under nitrogen
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-18992d5b1d194853917a545ca1899796
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Reaction notes

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