4-Carbamoyl-1-phenyl-pyridinium hydrochloride → 1-Phenylpiperidine-4-carboxamide

HRID 2233285

Reaction equation

HRID 2233285 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.CCO>[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 686786254-Carbamoyl-1-phenyl-pyridinium hydrochloride

Product 1

HCID 105843391-Phenylpiperidine-4-carboxamideYield 35.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 57419690EtOH EthanolSolvent

Procedure

2.0 g palladium on charcoal (10%) were added to a solution of 22.7 g 4-Carbamoyl-1-phenyl-pyridinium hydrochloride in 500 ml ethanol EtOH. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen at 3 bar for one hour. The catalyst was filtered off through a pad of celite and washed with ethanol. The filtrate was evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel with the eluent ethyl acetate:methanol=9:1=>4:1 to obtain 6.9 g 1-Phenyl-piperidine-4-carboxylic acid amide as a solid.

Workup

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. washwashed with ethanol
  3. customThe filtrate was evaporated in vacuo
  4. customThe resulting residue was purified by flash chromatography on silica gel with the eluent ethyl acetate

Sources & evidence

ORD record
ord-89dece25bbe4465f8c61ac5c56ea27e6
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Linked notes

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