Methanol → 1-[2-(6-Methyl-2-pyridyl)ethyl]-4-(4-methylsulfonylaminophenylsulfonyl)piperidine

HRID 1110920Notes

Reaction equation

HRID 1110920 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:22][C:23]1[N:28]=[C:27]([CH:29]=[CH2:30])[CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+].CO>O>[CH3:22][C:23]1[N:28]=[C:27]([CH2:29][CH2:30][N:19]2[CH2:20][CH2:21][CH:16]([S:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])=[CH:8][CH:9]=3)(=[O:15])=[O:14])[CH2:17][CH2:18]2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 707352-Ethenyl-6-methylpyridineHCID 517045Sodium AcetateHCID 185392394-(4-Methylsulfonylaminophenylsulfonyl)piperidine hydrochloride

Product 1

HCID 150277221-[2-(6-Methyl-2-pyridyl)ethyl]-4-(4-methylsulfonylaminophenylsulfonyl)piperidineYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.60 g (1.86 mmol) of 4-(4-methylsulfonylaminophenylsulfonyl)piperidine hydrochloride obtained in Example 5, 0.44 g (3.72 mmol) of 6-methyl-2-vinylpyridine and 0.31 g of sodium acetate were suspended in 10 ml of a mixture of methanol with water (1:1) and the suspension was refluxed for 2 h. The reaction liquid was filtered and the filtrate was concentrated to give a residue. After extraction with dichloromethane followed by washing with water, the organic layer was concentrated to precipitate white crystals. The crystals were collected by filtration and recrystallized from ethyl acetate to give 0.52 g (yield: 64%) of the intended compound.

Workup

  1. temperaturethe suspension was refluxed for 2 h
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customto give a residue
  6. extractionAfter extraction with dichloromethane
  7. washby washing with water
  8. concentrationthe organic layer was concentrated
  9. customto precipitate white crystals
  10. filtrationThe crystals were collected by filtration
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-22f4e91f05964c28ad710a2574a429fe
Source dataset
uspto-grants-1990_12
Patent number
US04977165

Reaction notes

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