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

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Reaction Conditions

Reaction Steps

To a solution of 0.288 g (1.016 mmol) of 5-(6-phenylhexyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.11 g (1.2 mmol) of 50% aqueous dimethylamine and 0.10 g (1.2 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=2/1) to yield the desired product.

Provenance & Evidence