Benzeneethanamine, 3,4-bis(phenylmethoxy)-, hydrochloride (1:1) → N-[2-(3,4-dibenzyloxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine

Participants

Reaction Steps

2.61 g of 3,4-dibenzyloxyphenethylamine hydrochloride and 2.70 g of 3-(3'-oxobutyl)benzamide were dissolved in 50 ml of methanol, to which was added 0.47 g of sodium cyanoborohydride. The reaction was allowed to stand at room temperature for 15 hours. Then, the solvent was distilled off and the residue was extracted with 300 ml of ethyl acetate. The organic phase was washed with water and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to silica gel chromatography (solvent chloroform:ethanol:acetic acid=90:8:2) to obtain 2.91 g of N-[2-(3,4-dibenzyloxyphenyl)ethyl]-1-methyl-3-(3-carbamoylphenyl)propylamine as a viscous oil.

Provenance & Evidence