Allylamine → HCID 19600254, compound

Participants

Reaction Steps

A solution of 6.019 g (62.64 mmol) of 3-furaldehyde and 5.37 g (94.0 mmol) of allylamine in 100 ml of methanol was stirred at room temperature for 0.5 hours. To this reaction mixture, 4.74 g (125 mmol) of sodium borohydride was added portionwise under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into an 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=1/1 to ethyl acetate) to yield N-allyl-3-furylmethylamine.

Provenance & Evidence