Benzaldehyde → (+)-Benzylphenethylamine

HRID 1016714Notes

Reaction equation

HRID 1016714 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H][H]>[Pd].CO>[CH2:10]([NH:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 6431891-Phenethylamine, (+)-HCID 178418361HCID 178418361, compound

Product 1

HCID 1268086(+)-Benzylphenethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

412 kg of methanol and 375.7 kg of (R)-1-phenylethylamine (ee=97.1%) are initially taken and 329 kg of benzaldehyde are added dropwise at 24° C. in the course of 120 minutes. Stirring is effected for 6 hours at 24° C., the completeness of the iminization is checked by GC, 6 kg of Pd/C (5% by weight) are added and the crude mixture is hydrogenated with hydrogen for 24 hours at atmospheric pressure. The sample is taken and the composition is investigated by GC analysis.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-c2ed1b962be84638b4f0356430de36ac
Source dataset
uspto-grants-2002_11
Patent number
US06476268B1

Reaction notes

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