Reaction #1171

Reaction equation

4-Piperidinecarboxamide

benzyl bromide

→

N-benzyl-4-piperidinecarboxamide

Yield 35.0%

Solvents

EtOAc

DMSO

Conditions

Workup

1. 1
   Washwashed with 1N aq. HCl, 5N aq. NaOH
2. 2
   Dryingdried over MgSO4
3. 3
   Concentrationconcentrated

Procedure

4-Piperidinecarboxamide (10.2 g, 78.0 mmol) in DMSO (10 mL) was treated with benzyl bromide (20.0 mL, 168 mmol). The mixture was diluted with EtOAc and washed with 1N aq. HCl, 5N aq. NaOH, dried over MgSO4, and concentrated to give 5.90 g (35%) of N-benzyl-4-piperidinecarboxamide. [1H]-NMR(CDCl3) consistent with structure.

Source