4-Piperidinecarboxamide → 1-Benzylpiperidine-4-carboxamide

HRID 849332Notes

Reaction equation

HRID 849332 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:17][CH2:16][CH:12]([C:13]([NH2:15])=[O:14])[CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:9]1[CH2:17][CH2:16][CH:12]([C:13](=[O:14])[NH2:15])[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 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 7831561-Benzylpiperidine-4-carboxamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

85.5 g of benzyl bromide are added dropwise at RT to a mixture of 58.2 g of isonipecotamide and 69 g of K2CO3 in 275 ml of DMF and the reaction mixture is stirred for 2 hours at 50° C. It is concentrated under vacuum, the residue is taken up with water and extracted with DCM, the organic phase is washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 62 g of the expected product after crystallization from 300 ml of water and drying under vacuum.

Workup

  1. concentrationIt is concentrated under vacuum
  2. extractionextracted with DCM
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-67eb23d0144f491fa9b34054c4fe6a70
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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