General procedure for the synthesis of N-(3-chloropropyl)dibutylamine from 3-(dibutylamino)propan-1-ol: 3-(dibutylamino)propan-1-ol (2.230 mmol, 0.418 g) was dissolved in chloroform (5 mL), and thionyl chloride (4.460 mmol, 0.328 mL) was slowly added via syringe. The reaction mixture was stirred under reflux conditions for 7 hours. After completion of the reaction, the reaction mixture was diluted with water and dichloromethane and potassium carbonate (1.2 g) was added. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate (5 mL) and water (5 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed in vacuum to afford N-(3-chloropropyl)dibutylamine as a yellow oil (0.430 g, 94% yield).1H NMR (400 MHz, CDCl3) δ 3.62 (t, J = 6.5 Hz, 1H), 2.55 (t, J = 6.8 Hz, 1H), 2.40 (t, 2H) 1.89 (qi, 1H), 1.48-1.36 (m, 2H), 1.36-1.26 (m, 2H), 0.93 (t, J = 7.3 Hz, 3H).13C NMR (101 MHz, CDCl3) δ 54.02, 51.06, 43.45, 30.61, 29.43, 20.67, 14.05. HRMS (EI+): m/z C11H24NCl calculated value: 205.1597, measured value: 205.1596.
