N-Methylbenzylamine → Ethyl 7-[benzyl(methyl)amino]heptanoate

Participants

Reaction Steps

Ethyl 7-bromoheptanoate (6.00 g, 25.3 mmol) was dissolved in acetonitrile (30 mL), N-methyl-benzylamine (6.53 mL, 50.6 mmol) and potassium carbonate (13.99 g, 101 mmol) were added at room temperature, and the mixture was heated to reflux for 6 hours. The mixture was left to stand for cooling, and the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give crude ethyl 7-[benzyl(methyl)amino]heptanoate (11.5 g) as a light yellow oily substance. The resulting crude product was dissolved in 60 mL of ethanol, 10% palladium-carbon (0.72 g) was added, and the mixture was stirred at 60° C. under a hydrogen atmosphere for 16 hours. The mixture was left to stand for cooling, insoluble matter was removed by filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by NH silica gel chromatography (ethyl acetate:methanol=10:0→10/1, v/v) to give the title compound (4.67 g; yield, 98%) as a colorless oily substance.

Provenance & Evidence