Thionyl Chloride → HCID 22678758, compound

HRID 1837746Notes

Reaction equation

HRID 1837746 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[O:23])[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O>C(O)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[O:23])[C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22678342HCID 22678342, compound

Product 1

HCID 22678758HCID 22678758, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.6 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-oxo-2-(2-thienyl)ethyl]piperidine obtained in Example 54 and 8.5 ml of thionyl chloride were dissolved in 60 ml of ethanol, and the mixture was heated under reflux for 3 hours. The solvent was evaporated, and then the residue was dissolved in chloroform and a 1N aqueous sodium hydroxide. The organic layer was separated, washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was recrystallized from ethanol, to give 9.0 g of the title compound as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in chloroform
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-9e68929ff4e54137ac28b0637553d1ab
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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