Ammonia → Homoveratrylamine

HRID 1704234Notes

Reaction equation

HRID 1704234 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][C:7]#[N:8].N>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH2:8])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 667273,4-Dimethoxybenzeneacetonitrile

Product 1

HCID 8421Homoveratrylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

100 kg. of crystalline 3,4-dimethoxy-benzyl cyanide are hydrogenated in 310 1. of a 80 to 96% aqueous ethanol containing 9 to 12% of ammonia in the presence of 24 kg. of Raney-nickel catalyst pre-treated as described in Example 3 at 48°-60° C under a hydrogen overpressure of 8 to 10 atm. The catalyst is filtered off, the filtrate is evaporated and the residue is subjected to fractionation in vacuo. Thus 95,5 kg. of highly pure 3,4-dimethoxy-beta-phenyl-ethylamine are obtained, purity: nearly 100%. The mono-demethylated beta-phenyl-ethylamine derivative impurity is present at most in traces in such a small amount, which can not be detected by thin layer chromatography.

Workup

  1. customas described in Example 3 at 48°-60° C under a hydrogen overpressure of 8 to 10 atm
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-f62ae4c6e8854921aadeb629cf79f646
Source dataset
uspto-grants-1978_11
Patent number
US04126615

Reaction notes

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