Ethylamine → 2-(4-Chloro-phenyl)-N-ethyl-acetamide

Participants

Reaction Steps

A mixture of 4-chlorophenyl acetic acid (1 g, 5.88 mmol), ethylamine (2M in tetrahydrofuran, 5.88 mL, 11.76 mmol), 1-hydroxybenzotriazole hydrate (90 mg, 5.88 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.13 g, 5.88 mmol), and triethylamine 1.78 g, 17.64 mmol) in dichloromethane (30 mL) was stirred at room temperature for 18 hours. The mixture was then diluted with 1M sodium hydroxide solution (30 mL) and the aqueous layer was extracted with dichloromethane (30 mL). The combined organic solution was washed with 1M hydrochloric acid and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 90:10, to afford the title compound as a colourless solid in 37% yield, 443 mg. 1H NMR (400 MHz, CDCl3) δ: 7.31-7.28 (2H, m), 7.27-7.24 (2H, m), 3.45 (2H, s), 3.18 (2H, m), 1.08 (3H, t) ppm; LRMS APCI m/z 198 [M+H]+

Provenance & Evidence