Ethanol → Ethyl 3-methylpiperidine-4-carboxylate hydrochloride

Reaction equation

Cl.[CH3:2][CH:3]1[CH:8]([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][NH:5][CH2:4]1.O=S(Cl)[Cl:14].[CH3:16][CH2:17]O>>[ClH:14].[CH3:2][CH:3]1[CH:8]([C:9]([O:11][CH2:16][CH3:17])=[O:10])[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

Reactant 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 691690773-Methylpiperidine-4-carboxylic acid hydrochloride

Product 1

HCID 51358495Ethyl 3-methylpiperidine-4-carboxylate hydrochloride

Procedure

The mixture of 3-methylpiperidine-4-carboxylic acid hydrochloride (3.3 g, 18.4 mmol, 1.0 eq) and SOCl2 (6.6 g, 55.3 mmol, 3.0 equiv) in EtOH (30 mL) was stirred at reflux for 3 h, and then the reaction mixture was concentrated by vacuum to give compound ethyl 3-methylpiperidine-4-carboxylate hydrochloride as a yellow oil which was used for next step. ESI-MS (M+H)+: 172.2.