Thionyl Chloride → N1-(3-Fluorobenzyl)-2-[1-[2-(2-oxo-1,2-dihydro-3-pyridinyl)ethyl]-2-piperidyl]acetamide

HRID 1837757Notes

Reaction equation

HRID 1837757 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][NH:6][C:7](=[O:25])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][C:17]1[C:18]([O:23]C)=[N:19][CH:20]=[CH:21][CH:22]=1.S(Cl)(Cl)=O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][NH:6][C:7](=[O:25])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[CH2:15][CH2:16][C:17]1[C:18](=[O:23])[NH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22678505N1-(3-Fluorobenzyl)-2-[1-[2-(2-methoxy-3-pyridyl)ethyl]-2-piperidyl]acetamide

Product 1

HCID 22678298N1-(3-Fluorobenzyl)-2-[1-[2-(2-oxo-1,2-dihydro-3-pyridinyl)ethyl]-2-piperidyl]acetamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

370 mg of N1-(3-fluorobenzyl)-2-[1-[2-(2-methoxy-3-pyridyl)ethyl]-2-piperidyl]acetamide obtained in Example 177, 0.44 ml of thionyl chloride and 5 ml of ethanol were stirred at 100° C. for 2 hours. The solvent was evaporated, and to the residue was added an aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, and dried over sodium sulfate. Then the drying agent was filtered off, and the solvent was evaporated, to give 330 mg of white crystals.

Workup

  1. customThe solvent was evaporated
  2. additionto the residue was added an aqueous sodium bicarbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationThen the drying agent was filtered off
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f0106358b0ce410aafc4537250399776
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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