HCID 10659313, compound → HCID 10489880, compound

HRID 964003Notes

Reaction equation

HRID 964003 reaction equation
[Cl-].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])[NH2:3].[H][H]>CO.[Pd]>[CH3:18][O:17][C:14]1[CH:13]=[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]=1

Participants

5

Reactant 2

HCID 10659313HCID 10659313, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10489880HCID 10489880, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-carbamoyl-1-(4-methoxyphenyl)-pyridinium chloride (22.0 g) in methanol (250 ml) was hydrogenated at ambient temperature and pressure in the presence of 10% palladium-on-carbon catalyst (1.0 g) for 2 days. Further catalyst (0.75 g) was added, and when no more hydrogen was taken up, the catalyst was removed by filtration. The filtrate was basified by the addition of an excess of triethylamine and the solvent removed in vacua. The residue was partitioned between water and a 19:1 mixture of chloroform and methanol. The solvent was removed in vacuo from the organic layer and the residue dried in vacuo over phosphorus pentoxide to give 1-(4-methoxyphenyl)piperidine-4-carboxamide as a white solid (10 g), m.p. 178°-181° C.

Workup

  1. customwas hydrogenated at ambient temperature
  2. customthe catalyst was removed by filtration
  3. additionThe filtrate was basified by the addition of an excess of triethylamine
  4. customthe solvent removed in vacua
  5. customThe residue was partitioned between water
  6. additiona 19:1 mixture of chloroform and methanol
  7. customThe solvent was removed in vacuo from the organic layer
  8. dry with materialthe residue dried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-4cecf59262bd46c7809b99836814d8bd
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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