Propargyl bromide → 1-(Prop-2-yn-1-yl)piperidine

Participants

Reaction Steps

Prepared using methodology as described in US 2005/0026944. To a stirred mixture of piperidine (851 mg, 10.0 mmol), cesium carbonate (3.26 g, 10.0 mmol) and acetone (20 mL) was added 3-bromoprop-1-yne (1.49 g, 10.0 mmol; 80% in toluene) at room temperature. The white suspension was stirred for 18 hours at room temperature. The suspension was filtered, and the filtrate was concentrated. The resulting residue was triturated with diethyl ether (10 mL), filtered, and the filtrate concentrated to obtain the product as an oil (0.70 g, 56%). 1H NMR (400 MHz, CDCl3) δ 3.27 (d, J=2 Hz, 2H), 2.50 (m, 4H), 2.22 (t, J=2 Hz, 1H), 1.62 (m, J=6 Hz, 4H), 1.43 (m, 2H).

Provenance & Evidence