3-Furaldehyde → N-(3-furylmethyl)-6-phenylhexylamine

Participants

Reaction Steps

A solution of 9.138 g (29.73 mmol) of N-(6-phenylhexyl)phthalimide and 2.16 ml (44.6 mmol) of hydrazine monohydrate in 100 ml of ethanol was refluxed for 1 hour. After cooling to room temperature, the 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 6-phenylhexylamine was dissolved in 100 ml of methanol; 2.86 g (29.7 mmol) of 3-furaldehyde was added, followed by stirring at room temperature for 0.5 hours, after which 2.25 g (59.5 mmol) of sodium borohydride was added under ice-cooling, followed by stirring at room temperature for 1 hour. The 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 crude product was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to yield the desired product.

Provenance & Evidence