Acetic Acid → 1-Benzhydryl-3-ethylaminoazetidine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-benzhydrylazetidin-3-one (9.5 g, 40 mmol) in methanol (30 ml) was added ethylamine hydrochloride (4.2 g, 52 mmol) and then acetic acid (3.0 ml, 52 mmol) at room temperature. After stirring for 15 minutes, solid KCN (3.4 g, 52 mmol) was added and the homogeneous mixture was heated at 60° C., overnight. The reaction was cooled and then concentrated, in vacuo. The residue was then extracted from saturated aqueous sodium bicarbonate with ethyl acetate, the combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo, to afford I-(13A-9)d as a colorless solid (11.7 g, quantitative): +ES MS (M+1) 292.2; 1H NMR (400 MHz, CD3OD) δ 7.42 (d, J=7.5 Hz, 4H), 7.26 (t, J=7.5 Hz, 4H), 7.17 (t, J=7.3 Hz, 2H), 4.47 (s, 1H), 3.54 (d, J=8.3 Hz, 2H), 3.25 (d, J=8.3 Hz, 2H), 2.61 (s, J=7.2 Hz, 2H), 1.11 (t, J=7.3 Hz, 3H).

Provenance & Evidence