Ammonium formate → 1-(Pyridin-2-yl)piperazin-2-one

HRID 2213049Notes

Reaction equation

HRID 2213049 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[C:10](=[O:20])[CH2:9]2)C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].O.CO>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C:10]1=[O:20]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 21955123HCID 21955123, compound

Product 1

HCID 218650171-(Pyridin-2-yl)piperazin-2-oneYield 46.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A slurry of palladium on carbon (5%, 3.6 g) in water was added to a solution of 4-phenylmethyl-1-(2-pyridinyl)piperazin-2-one (Description 150, 3.6 g, 13.48 mmol) and ammonium formate (4.25 g, 67.5 mmol) in methanol (100 mL) and the mixture was heated under reflux for 4 hours, cooled and filtered through Hyflo™, washing with methanol. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel eluting with CH2Cl2/MeOH (90:10), to give the title compound as an orange oil (1.1 g, 46%). m/z (ES+) 178 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. filtrationfiltered through Hyflo™
  5. washwashing with methanol
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by flash column chromatography on silica gel eluting with CH2Cl2/MeOH (90:10)

Sources & evidence

ORD record
ord-69723cc44a3c44a99be509db4ba7ff0a
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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