Ammonia → 3-Phenoxy-benzylamine

HRID 224267Notes

Reaction equation

HRID 224267 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[H][H]>[Ni].CO>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH2:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 34141613-PhenoxybenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 10948363-Phenoxy-benzylamineYield 98.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

200 g (1.025 mols) of 3-phenoxybenzonitrile is placed together with 1 liter of methanol, 200 g of liquid ammonia and 50 g of Raney nickel into a steel autoclave. This is then heated to 60° C., and stirring is maintained for one hour with an initial hydrogen pressure of 120 bars. After removal of the mixture from the autoclave, the catalyst is filtered off, the solvent is distilled off at normal pressure, and the residue is distilled in an oil-pump vacuum to obtain 200.3 g (1.01 mols) of 3-phenoxybenzylamine (98.7% strength), corresponding to a yield of 94.7% of theory; b.p. 94° C./3 Pa; nD20 =1.5946.

Workup

  1. customAfter removal of the mixture from the autoclave
  2. filtrationthe catalyst is filtered off
  3. distillationthe solvent is distilled off at normal pressure
  4. distillationthe residue is distilled in an oil-pump vacuum

Sources & evidence

ORD record
ord-f10b8a45247e469786d6874d76546fc2
Source dataset
uspto-grants-1980_11
Patent number
US04231962

Reaction notes

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