Sodium Hydroxide → 2(1H)-Pyridinone, 3-((4-(2-(3-(methylsulfonyl)-2-thienyl)ethyl)-1-piperidinyl)methyl)-

HRID 1837745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837745
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][C:22]=3[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O.[OH-].[Na+]>C(O)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][C:22]=3[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 22678292HCID 22678292, Verbindung

Produkt 1

HCID 226782962(1H)-Pyridinone, 3-((4-(2-(3-(methylsulfonyl)-2-thienyl)ethyl)-1-piperidinyl)methyl)-Ausbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6.09 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(3-methylsulfonyl-2-thienyl)ethyl]piperidine obtained in Example 43 and 2 ml of thionyl chloride were dissolved in 50 ml of ethanol, and the mixture was heated under reflux for 2 hours. The reaction mixture was basified by adding a 1N aqueous sodium hydroxide thereto, and then extracted with dichloromethane. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified by NH form silica gel column chromatography (ethyl acetate), to give 4.89 g of the title compound as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting crude product was purified by NH
  8. customform silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-00ca5ea8d27945e7b67f204378a39566
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06784192B2

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