Formaldehyde → 1-(2-diethylaminomethyl-6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

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Reaction Conditions

Reaction Steps

To a solution of 0.347 g (1.167 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 0.14 ml (1.4 mmol) of diethylamine and 0.11 g (1.4 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1.5 hours. 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