2-(4-Chlorophenyl)ethylamine → N-[2-(4-chlorophenyl)ethyl]-2-(2-fluorophenyl)acetamide

Participants

Reaction Steps

2-Fluorophenylacetic acid (17 mg, 0.11 mmole) and 4-chlorophenethylamine (15 mg, 0.1 mmole) were dissolved in 5 ml dichloromethane. To this was added catalytic 4-dimethylaminopyridine (DMAP) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 33 mg, 0.11 mmole). The resulting solution was stirred at room temperature overnight. The reaction was then worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The compound was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 7.31-6.92 (m, 8H), 5.48 (bs, 1H), 3.51 (s, 2H), 3.42 (m, 2H), 2.70 (m, 2H).

Provenance & Evidence