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

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Reaction Conditions

Reaction Steps

To a solution of 0.250 g (0.824 mmol) of 6-(4-phenylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.112 ml (1.24 mmol) of 50% aqueous dimethylamine and 0.101 ml (1.24 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. Additionally, 0.075 ml (0.82 mmol) of 50% aqueous dimethylamine and 0.067 ml (0.82 mmol) of 37% aqueous formaldehyde were added, followed by stirring for 20 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous solution of 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