Dimethylamine → N,N-dimethyl-[6-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepin-2-ylmethyl]amine

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Reaction Conditions

Reaction Steps

To a solution of 0.179 g (0.518 mmol) of 6-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine in 20 ml of acetic acid, 56 mg (0.62 mmol) of 50% aqueous dimethylamine and 50 mg (0.62 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