Ammonia → 2-[4-(Trifluoromethoxy)phenyl]ethan-1-amine

HRID 2306164Notes

Reaction equation

HRID 2306164 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.N.[H][H]>[Ni].CO>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][NH2:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 1426764-(Trifluoromethoxy)phenylacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 106320402-[4-(Trifluoromethoxy)phenyl]ethan-1-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

650 ml of methanol, 260 g of (4-trifluoromethoxyphenyl)acetonitrile, and moist Raney nickel in an amount corresponding to 0.39 mol were initially charged in an autoclave, and 260 ml of ammonia were condensed in. The mixture was hydrogenated at 130° C. and a hydrogen pressure of 140 bar for 2 hours. The reaction mixture was then vented at room temperature, and the catalyst was filtered off. The filtrate was distilled at 10 hPa. This gave 224.5 g of 2-(4-trifluoromethoxyphenyl)ethylamine as a colorless liquid (86.7% of theory) of b.p. 84-86° C.

Workup

  1. customcondensed in
  2. customwas hydrogenated at 130° C.
  3. customwas then vented at room temperature
  4. filtrationthe catalyst was filtered off
  5. distillationThe filtrate was distilled at 10 hPa

Sources & evidence

ORD record
ord-bf724499115d4aee807d3dd83af1bacf
Source dataset
uspto-grants-2002_08
Patent number
US06441239B1

Reaction notes

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