The general procedure for the synthesis of N-hexadecylbenzamide from hexadecylamine and benzoyl chloride was as follows: benzoyl chloride (13.0 mL, 112 mmol) was dissolved in dichloromethane (200 mL) and the solution was cooled to 0°C in an ice bath. A second solution prepared from 1-hexadecylamine (30.8 g, 110 mmol) and triethylamine (17.0 mL, 122 mmol) in methylene chloride (300 mL) was added slowly and dropwise under nitrogen protection. The reaction mixture was stirred overnight at room temperature. Subsequently, the reaction products were washed sequentially with 10% aqueous hydrochloric acid solution (ethanol was added to avoid emulsification), saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate and filtered, and dichloromethane was removed by evaporation under reduced pressure to give the white solid product N-hexadecylbenzamide (30.1 g, 87.0 mmol, 93% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and HRMS (ESI+): 1H NMR δ= 7.75 (d, J = 8.4 Hz, 2H), 7.49 (t, J = 6.7 Hz, 1H), 7.42 (t, J = 7.3 Hz, 2H), 6.14 (s, 1H), 3.44 (dd, J = 13.1, 7.0 Hz, 2H), 1.74-1.50 (m, 2H), 1.25 (s, 26H), 0.88 (t, J = 6.8 Hz, 3H); HRMS (ESI+) C23H40NO [M + H]+: calculated value 346.3104, measured value 346.3107.
