Dimethylamine → 1-(2-dimethylaminomethyl-6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-2-(2-naphthoxy)ethan-1-one

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Reaction Conditions

Reaction Steps

To a solution of 0.200 g (0.651 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-2-(2-naphthoxy)ethan-1-one in 20 ml of acetic acid, 0.088 ml (0.98 mmol) of 50% aqueous dimethylamine and 0.079 ml (0.98 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide 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 (ethyl acetate/methanol=9/1 to 6/1) to yield the desired product.

Provenance & Evidence