Sodium Hydroxide → 351407-14-2

HRID 1837745Notes

Reaction equation

HRID 1837745 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[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

Participants

5

Reactant 3

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

Product 1

HCID 22678296351407-14-2Yield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-00ca5ea8d27945e7b67f204378a39566
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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