Ammonia → 2,4-Difluoro-benzenepropanamine

HRID 974396Notes

Reaction equation

HRID 974396 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]#[N:12].N.[H][H]>C(O)C.[Ni]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][NH2:12]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 183533953-(2,4-Difluorophenyl)propanenitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 226691392,4-Difluoro-benzenepropanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

33.4 g (0.20 mol) of 3-(2,4-difluorophenyl)propionitrile are dissolved in 200 ml of ethanol and, after 2.8 g of Raney nickel in ethanol have been added and after 34 g (2.0 mol) of ammonia gas have been injected, are hydrogenated using hydrogen gas in a pressurized reactor at 75°-80° C. The take-up of hydrogen is complete after about 3 hours. The reaction mixture is cooled, decompressed and filtered and then freed from solvent on a vacuum rotary evaporator. The resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar). 26.0 g (76% of theory) of a colourless oil are obtained.

Workup

  1. customat 75°-80° C
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customfreed from solvent on a vacuum rotary evaporator
  5. distillationThe resultant oil is subjected to fractional distillation at 89°-90° C. in vacuo (13 mbar)
  6. custom26.0 g (76% of theory) of a colourless oil are obtained

Sources & evidence

ORD record
ord-057595c8470e4e1b9924399ecaee847e
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

Loading…