4-Piperidinecarboxamide → 1-Benzylpiperidine-4-carboxamide

HRID 1265170Notes

Reaction equation

HRID 1265170 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 37724-PiperidinecarboxamideHCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 7831561-Benzylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 20 g (156 mmol) of isonipecotamide, 32.4 g (234 mmol) of potassium carbonate, 2 g (12 mmol) of potassium iodide and 18.6 ml (156 mmol) of benzyl bromide in 400 ml of acetonitrile is heated at reflux for 5 hours. The solvent is evaporated off and the residue is taken up in a dichloromethane/water mixture. After decanting, extracting with dichloromethane, washing the organic phases with brine and drying, removal of the solvent by evaporation yields the expected product.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent is evaporated off
  4. customAfter decanting
  5. extractionextracting with dichloromethane
  6. washwashing the organic phases with brine
  7. customdrying
  8. customremoval of the solvent
  9. customby evaporation

Sources & evidence

ORD record
ord-d8a1b06cf2fd4e39a0ec744db2393c0a
Source dataset
uspto-grants-2003_04
Patent number
US06545037B2

Reaction notes

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