4-Piperidinecarboxamide → 1-Benzylpiperidine-4-carboxamide

HRID 2300165Notes

Reaction equation

HRID 2300165 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O>[CH2:10]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 7831561-Benzylpiperidine-4-carboxamideYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 15 g 4-piperidinecarboxamide, 16.3 g benzyl chloride, 32.3 g potassium carbonate and 200 ml N,N-dimethylformamide was stirred at 80° C. for 4 hr. The reaction solution was returned to room temperature, and aqueous sodium hydroxide was added thereto, and then it was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then evaporated. The resulting crystalline residue was washed with hexane/ethyl acetate and collected by filtration. 12.7 g of 1-benzyl-4-piperidine carboxamide was obtained as white flaky crystals.

Workup

  1. customwas returned to room temperature
  2. extractionit was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. washThe resulting crystalline residue was washed with hexane/ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a921b215a15c47868f05d77bb4efe194
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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