N-Methylbenzylamine → N-Methylhomoveratrylamine

HRID 357700Notes

Reaction equation

HRID 357700 reaction equation
[CH2:1]([C:12]#[N:13])[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[H][H].[CH3:16]NCC1C=CC=CC=1>>[CH3:16][NH:13][CH2:12][CH2:1][C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

4

Reactant 3

HCID 7669N-MethylbenzylamineHCID 667273,4-DimethoxybenzeneacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 77039N-MethylhomoveratrylamineYield 70%

Procedure

205 ml of a 28% strength solution of veratryl cyanide in methylbenzylamine (molar ratio 1:3.7) were pumped each hour upwards through a vertical hydrogenation reactor (diameter: 16 mm; height of packing: 600 mm; oil-heated jacket) which was packed with 511 g (800 ml) of catalyst (0.5% by weight of palladium on alumina) at 160° C. under 200 bar. Simultaneously, 100 l(STP)/h hydrogen were passed upwards through the reactor. After decompression to atmospheric pressure, excess methylbenzylamine was removed by distillation, and the discharge was analyzed by quantitative gas chromatography. 40 g (70%) of N-methylhomoveratrylamine were obtained per hour.

Workup

  1. temperature(diameter: 16 mm; height of packing: 600 mm; oil-heated jacket) which
  2. customAfter decompression to atmospheric pressure, excess methylbenzylamine was removed by distillation

Sources & evidence

ORD record
ord-827b73205fd1472dbb8e9bab9f807e76
Source dataset
uspto-grants-1998_11
Patent number
US05840981

Reaction notes

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