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Sodium Hydroxide → 1-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidine

HRID 1837742
Notes
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Reaction equation

HRID 1837742 reaction equation
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[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([CH3:27])(=[O:26])=[O:25])[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[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([CH3:27])(=[O:26])=[O:25])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][NH:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 226785581-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidine

Product 1

HCID 226787401-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidineYield 79.7%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

479 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidine obtained in Example 1 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 the mixture was 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 silica gel column chromatography (ethyl acetate), to give 368 mg of the title compound as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted 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 silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-74ec9cf3de53440eb6132058cd2eb88e
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06784192B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes