Water → (4-Hydroxy-4-methylpiperidin-1-yl)(5-methyl-2-(pyridin-4-yl)phenyl)methanone

HRID 538455

Reaktionsgleichung

Reaktionsgleichung von HRID 538455
C[Mg]Br.[CH2:4](OCC)C.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[C:14]([CH:24]=1)[C:15]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)=[O:16].O>C1COCC1>[OH:23][C:20]1([CH3:4])[CH2:19][CH2:18][N:17]([C:15]([C:14]2[CH:24]=[C:10]([CH3:9])[CH:11]=[CH:12][C:13]=2[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[O:16])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 866808481-(5-Methyl-2-(pyridin-4-yl)benzoyl)piperidin-4-oneHCID 178467822HCID 178467822, Verbindung

Produkt 1

HCID 86680849(4-Hydroxy-4-methylpiperidin-1-yl)(5-methyl-2-(pyridin-4-yl)phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3 M methylmagnesium bromide-diethyl ether solution (0.84 mL) was added to a solution of 1-(5-methyl-2-(pyridin-4-yl)benzoyl)piperidin-4-one (0.37 g) in THF (10 mL) at 0° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added water at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (0.19 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4764233ed4654eb6a043f405c4eeb687
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865717B2

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