Sodium Hydroxide → 5-(6-Phenylhexyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

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Reaction Steps

To a solution of 1.533 g (4.793 mmol) of N-(2-chloroethyl)-N-(3-furylmethyl)-6-phenylhexylamine in 100 ml of tetrahydrofuran, 8.99 ml (14.4 mmol) of 1.6 M n-butyl lithium in hexane was added under ice-cooling, followed by stirring at room temperature for 4 hours. This reaction mixture was poured into 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 (hexane/ethyl acetate=9/1) to yield the desired product.

Provenance & Evidence