Thionyl Chloride → tert-Butyl 4-(Chlorocarbonyl)piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([Cl:19])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (1.000 g, 4.00 mmol) in chloroform (15 mL) was added thionyl chloride (3.0 mL, 40.00 mmol). The reaction mixture was left stirring at reflux for 3 days and then concentrated in vacuo. The obtained crude solid, 4-chlorocarbonylpiperidine-1-carboxylic acid tert-butyl ester, was used without further purification.