4-Carbamoyl-1-(3-methoxyphenyl)pyridinium chloride → 1-(3-Methoxyphenyl)piperidine-4-carboxamide

HRID 964006

Reaction equation

HRID 964006 reaction equation
[Cl-].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])[NH2:3].[H][H]>CO.[Pd]>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([N:8]2[CH2:9][CH2:10][CH:5]([C:2]([NH2:3])=[O:4])[CH2:6][CH2:7]2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 106116954-Carbamoyl-1-(3-methoxyphenyl)pyridinium chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 106097471-(3-Methoxyphenyl)piperidine-4-carboxamideYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-carbamoyl-1-(3-methoxyphenyl)-pyridinium chloride (26 g) in methanol (300 ml) was hydrogenated at ambient temperature and pressure in the presence of 10% palladium-on-carbon catalyst (2.0 g) until hydrogen uptake ceased (~2 days) The mixture was filtered, excess triethylamine added and the solvent removed in vacuo to give a pink solid. This was partitioned between water and chloroform. The organic phase was dried and the solvent removed in vacuo to give 1-(3-methoxyphenyl)piperidine-4-carboxamide as a pink solid (19 g), m.p. 153°-156° C.

Workup

  1. customwas hydrogenated at ambient temperature
  2. custom(~2 days)
  3. filtrationwas filtered
  4. additionexcess triethylamine added
  5. customthe solvent removed in vacuo
  6. customto give a pink solid
  7. customThis was partitioned between water and chloroform
  8. customThe organic phase was dried
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-77d34deed1904da48785faccfa985f19
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Linked notes

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