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

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.230 g (0.694 mmol) of 5-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.094 ml (1.04 mmol) of 50% aqueous dimethylamine and 0.085 ml (1.04 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1); the resulting solid was washed with hexane to yield the desired product.

Provenance & Evidence