1-Chloroethyl chloroformate → HCID 58772391, compound

Participants

Reaction Steps

To a stirred solution of 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-4-fluoro-piperidine 4c (13.8 g, 0.04 mol) in dichloromethane (50 mL) was added 1-chloroethylchloroformate. (7.1 g, 0.05 mol). The mixture was stirred at room temperature for 2 h and then concentrated to dryness. The residual was dissolved in methanol (50 mL) and then heated to reflux for 30 min. The mixture was concentrated to dryness in vacuo, ether was added, the precipitate solid was filtered and washed with ether to obtain 4-(5-chloro-2-methoxyphenyl)-4-fluoropiperidine 4d as its hydrochloride salt. 1H NMR (DMSO-d6): δ 9.10-9.01 (m, 2H), 7.25 (q, J1=8.4 Hz, J2=8.8 Hz, 1H), 7.33 (d, J=2.8 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H), 3.82 (s, 3H), 3.27 (s, 2H), 3.13-3.04 (m, 2H), 2.79-2.66 (m, 2H), 1.924-1.864 (t. 2H). MS (ESI) m/z (M+H+) 243.98.

Provenance & Evidence