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

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Reaction Conditions

Reaction Steps

To a solution of 0.280 g (0.784 mmol) of 6-(anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.106 ml (1.18 mmol) of 50% aqueous dimethylamine and 0.096 ml (1.18 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 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 yield the desired product.

Provenance & Evidence