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

HRID 539666

Reaction equation

HRID 539666 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fc54a69d301e43418919d9befc9c94dd
Source dataset
uspto-grants-2014_10
Patent number
US08871766B2

Linked notes

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