Benzylamine → 6-Benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

Participants

Reaction Steps

To a solution of 1.208 g (7.735 mmol) of 2-[3-(2-hydroxyethyl)furan-2-yl]ethanol and 4.04 ml (23.2 mmol) of N,N-diisopropylethylamine in 50 ml of dichloromethane, 1.32 ml (17.0 mmol) of methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 100 ml of ethanol; 0.83 g (7.7 mmol) of benzylamine and 2.37 ml (17.0 mmol) of triethylamine were added, followed by stirring at 80° C. for 3 days. After the solvent was distilled off from the reaction mixture under reduced pressure, aqueous sodium hydroxide was added, followed by 3 extractions with ethyl acetate. 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