Dimethylamine → 1-(2-Dimethylaminomethyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

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Reaction Conditions

Reaction Steps

To a solution of 0.230 g (0.739 mmol) of 1-(4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 80 mg (0.89 mmol) of 50% aqueous dimethylamine and 72 mg (0.89 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 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