Thionyl Chloride → 1-Diphenylmethyl-4-chloromethylpiperidine

Participants

Reaction Steps

Step 2): SOCl2 (0.6 ml, 8.2 mmol) was added dropwise to a solution of 1-diphenylmethyl-4-hydroxymethylpiperidine (1.0 g, 3.6 mmol) in benzene (7 ml) at room temperature. The mixture was refluxed for 18 hours and then concentrated. The residue was dissolved in ethyl acetate, washed with 5% NaOH solution, dried (MgSO4) and concentrated. The residue was recrystallized (ethyl acetate/ether/hexane) to give 1-diphenylmethyl-4-chloromethylpiperidine (70.1%): mp 73°-75° C.

Provenance & Evidence