Dimethylamine → N,N-dimethyl-[5-(4-phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.218 g (about 0.728 mmol) of the above 5-(4-phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.08 g (0.9 mmol) of 50% aqueous dimethylamine and 0.07 g (0.9 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 15 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

Provenance & Evidence