4-Piperidinecarboxamide → N-benzylpiperidine-4-carboxamide

HRID 1075

Reaction equation

HRID 1075 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O.CCOC(C)=O>[CH2:10]([NH:9][C:7]([CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 37724-PiperidinecarboxamideHCID 7498Benzyl Bromide

Product 1

HCID 3868064N-benzylpiperidine-4-carboxamideYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. washwashed with 1N aq. HCl, 5N aq. NaOH
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aad08f27e18e4070affc2570d3f9689b
Source dataset
uspto-grants-1998_03
Patent number
US05723490

Linked notes

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