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

HRID 2213049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213049
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]

Komponenten

6

Edukt 2

HCID 2723923Ammonium formateHCID 21955123HCID 21955123, Verbindung

Produkt 1

HCID 218650171-(Pyridin-2-yl)piperazin-2-oneAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-69723cc44a3c44a99be509db4ba7ff0a
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105507B2

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