4-Carbamoyl-1-phenylpyridinium chloride → 1-Phenylpiperidine-4-carboxamide

HRID 963998Notes

Reaction equation

HRID 963998 reaction equation
[Cl-].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])[NH2:3]>[Pd].C(O)C>[C:11]1([N:8]2[CH2:9][CH2:10][CH:5]([C:2]([NH2:3])=[O:4])[CH2:6][CH2:7]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 107048844-Carbamoyl-1-phenylpyridinium chloride

Product 1

HCID 105843391-Phenylpiperidine-4-carboxamideYield 52.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-carbamoyl-1-phenylpyridinium chloride (13 g), 10% palladium-on-carbon catalyst (260 mg) and ethanol (250 ml) was hydrogenated at ambient temperature and pressure for 2 days. The solution was filtered (Celite) and the filtrate was concentrated to approximately 50 ml. This solution was cooled and the solid precipitate collected by filtration to give 1-phenylpiperidine-4-carboxamide (5.99 g).

Workup

  1. customwas hydrogenated at ambient temperature
  2. filtrationThe solution was filtered (Celite)
  3. concentrationthe filtrate was concentrated to approximately 50 ml
  4. temperatureThis solution was cooled
  5. filtrationthe solid precipitate collected by filtration

Sources & evidence

ORD record
ord-a11b4d6683ae48778c67323737e82d03
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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