Veratraldehyde → (R)-(+)-(3,4-Dimethoxy)benzyl-1-phenylethylamine

Participants

Reaction Conditions

Reaction Steps

Veratraldehyde (174.5 g, 1.05 mole) was dissolved in isopropanol (600 ml) at 10-40° C. and (R)-1-phenylethylamine (121.2 g, 1.00 mmole) was added at 50-60° C. over 1-2 hr in a thin stream. Further, after stirring at 50-60° C. for 1-2 hr, the mixture was cooled to 20° C. To this solution were added triethylamine (5.1 g, 50.0 mmole) and 5% palladium carbon (50% wet, 5.4 g) at 20-30° C. and the mixture was stirred under 1 atm hydrogen atmosphere at 40-45° C. for 7-8 hr. The catalyst was filtered off and the filtrate was concentrated to give the title compound (277.5 g, pure amount 252.5 g, yield 93.05%) (Quantitative analysis by HPLC).

Provenance & Evidence