Hydrochloric Acid → {[8-(2-chlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride

Participants

Reaction Steps

To a solution of 2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman (170 mg, 0.535 mmol) in tetrahydrofuran (5 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.535 g, 1.605 mmol) and the reaction mixture stirred at room temperature for 24 hours. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under reduced pressure to afford a yellow syrup. The product was dissolved in 2-propanol (1 mL) and diethyl ether (2 mL) and a solution of hydrogen chloride (1.0 M in diethyl ether, 0.51 mL, 0.51 mmol) added followed hexane (4 mL). The resulting white precipitate was filtered to afford 118 mg (67%) of {[8-(2-chlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride as a white solid. HRMS: calcd for C16H15ClFNO+H+, 292.08990. found (ESI, [M+H]+), 292.0903.

Provenance & Evidence