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

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Reaction Steps

To a solution of 0.228 g (0.900 mmol) of the above N,N-dimethyl-(4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl)amine dihydrochloride, 0.24 g (1.1 mmol) of 2-benzoylbenzoic acid and 0.50 ml (3.6 mmol) of triethylamine in 30 ml of dichloromethane, 0.22 g (1.35 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 2 times. The combined organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (chloroform to chloroform/methanol=25/1) to yield the desired product.

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