Whitby group

To a stirred solution of N-methylallylamine (710 mg, 10.0 mmol), K₂CO₃ (2.00 g, 20.0 mmol) and MeCN (20 mL), cinnamyl bromide (1.97 g, 10.0 mmol) was added dropwise at 0 °C.  The solution was allowed to warm to room temperature, refluxed for 1 hour, before quenching with a saturated solution of NaHCO₃ (50.0 mL).  The product was extracted into diethyl ether (3 x 40 mL), the combined organic layer washed with water (3 x 30 mL), brine (50.0 mL), dried over MgSO₄, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO₂, 0-100 % Et₂O:petroleum including 5 % Et₃N) afforded the title compound as an orange oil (1.71 g, 9.1 mmol, 91 %).