Benzylamine → N-Benzylbut-3-en-1-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of benzylamine (100 mL, 0.9 mol) and 4-bromobut-1-ene (25 g, 0.18 mmol) in ethanol (250 mL) was added sodium iodide (1.0 g, 6.7 mmol). The reaction mixture was degassed via argon bubbling for 20 min then heated to 75° C. for 4 h. After cooling, the reaction mixture was diluted with dichloromethane (1 L) and 1M KOH (500 mL) was added. The two phases were separated and the aqueous layer was further extracted with dichloromethane (3×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, ethyl acetate to 10:1 ethyl acetate/triethylamine) provided N-benzylbut-3-en-1-amine (24.5 g, 84%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.31-7.28 (m, 3H), 7.24-7.21 (m, 2H), 5.82-5.72 (m, 1H), 5.10-5.00 (m, 2H), 3.77 (s, 2H), 2.68 (t, J=6.8 Hz, 2H), 2.29-2.23 (m, 2H), 1.36 (br s, 1H).

Provenance & Evidence