4-Piperidinecarboxamide → 1-Benzylpiperidine-4-carboxamide

HRID 239105

Reaction equation

HRID 239105 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 7831561-Benzylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.2 mL benzylchloride was added to 10 g piperidine-4-carboxylic acid amide and 21.6 g potassiumcarbonate in 280 mL DMF at 5° C. The reaction was stirred over night at RT. The solvent was removed and the residue was dissolved in water and dichlormethane. The organic layer was separated and evaporated. The residue was purified by column chromatographie (silica gel, eluent: dichlormethane/methanol 95:5 to 90:10) to give 9.8 g of the desired product.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in water
  3. customThe organic layer was separated
  4. customevaporated
  5. customThe residue was purified by column chromatographie (silica gel, eluent: dichlormethane/methanol 95:5 to 90:10)

Sources & evidence

ORD record
ord-d51ef4104a7f48138255f28aebcc2c3c
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Linked notes

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