Trifluoroacetic acid → HCID 9816269, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of (4E)-N-methyl-N-(tert-butoxycarbonyl)-5-(3,4-dichlorophenyl)-4-penten-2-amine (1.38 g, 4.01 mmol) in anisole (20 mL) was treated drop-wise over 45 min with trifluoroacetic acid (20.72 g, 181.7 mmol). The resulting solution was stirred for 1.5 h at 0-5° C. The solution was then concentrated by rotary evaporation followed by further drying under high vacuum. The resulting residue was cooled (0-5° C.), basified with 10% NaOH solution (15 mL), treated with saturated NaCl solution (10 mL) and extracted with CHCl3 (6×20 mL). The combined CHCl3 extracts were washed with saturated NaCl solution (25 mL), dried (Na2SO4), filtered, concentrated by rotary evaporation, followed by further drying under high vacuum to produce a light-brown oil (0.96 g). The crude product was purified by column chromatography on silica gel (50 g), eluting with CH3OH—Et3N (98:2, v/v). Selected fractions containing the product (Rf 0.44) were combined and concentrated on a rotary evaporator. The residue was dissolved in CHCl3. The CHCl3 solution was dried (Na2SO4), filtered, concentrated by rotary evaporation and dried under high vacuum to give 467 mg (47.7%) of a light-yellow oil.

Provenance & Evidence