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

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Reaction Conditions

Reaction Steps

To a solution of 0.200 g (0.604 mmol) of 5-(3-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.082 ml (0.91 mmol) of 50% aqueous dimethylamine and 0.073 ml (0.73 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. 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 to 25/1) to yield the desired product.

Provenance & Evidence