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

HRID 1090956

Reaktionsgleichung

Reaktionsgleichung von HRID 1090956
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bc76334c947d411dad1abc35c67b41bb
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082850

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