1-Chloroethyl chloroformate → Hydrochloric Acid

Participants

Reaction Steps

To a solution of 1-benzyl-4-(2-methoxy-phenyl)-piperidine-4-carbonitrile 7a (6.17 g, 0.02 mol) in CH2Cl2 (200 mL) was added dropwise chloroformic acid 1-chloroethyl ester (3.66 g, 0.03 mol). After stirred for 5 h the mixture was concentrated under reduced pressure and methanol (200 mL) was added. The mixture was then heated to reflux for 30 min. The solvent was removed under vacuum. Diethyl ether (100 mL) was added and the white precipitate was collected by filtration to afford 4-(2-methoxyphenyl)piperidine-4-carbonitrile 7b as HCl salt. 1H NMR (CDCl3) δ 9.5-9.1 (br, 2H), 7.41 (t, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.02 (t, J=7.6 Hz, 1H), 3.87 (s, 3H). 3.44 (d, J=13.2 Hz, 2H), 3.08 (m, 2H), 2.48 (m, 2H), 2.28 (m, 2H). MS (ESI) m/z (M+H+) 217.2.

Provenance & Evidence