N-Phenylisonicotinamide → N-Phenyl-4-piperidinecarboxamide

HRID 1389151

Reaction equation

HRID 1389151 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt]=O>[C:1]1([NH:7][C:8]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 220840N-Phenylisonicotinamide

Product 1

HCID 590499N-Phenyl-4-piperidinecarboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

4-(N-phenylcarbamoyl)pyridine [75.0 g, prepared as in Chem. Abs., 2013h (1958)] was hydrogenated in acetic acid (800 ml) using a platinum oxide catalyst at 50 p.s.i./30°. The catalyst was then removed by filtration, the solution evaporated, the residue basified to about pH 12 with sodium hydroxide, extracted with chloroform, and the organic extract discarded. The aqueous phase was evaporated to dryness, the residue boiled with chloroform, filtered and evaporated to leave 4-(N-phenylcarbamoyl)piperidine (17.0 g), m.p. 121°-127°. The hydrochloride salt, m.p. 231°-233°, was prepared in isopropanol from the free base and hydrogen chloride, and was recrystallised from isopropanol/ethyl acetate.

Workup

  1. custom30°
  2. customThe catalyst was then removed by filtration
  3. customthe solution evaporated
  4. extractionextracted with chloroform
  5. extractionthe organic extract
  6. customThe aqueous phase was evaporated to dryness
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ed91d820945c4c76a1e29bdf3346ec42
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Linked notes

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