Sodium Carbonate → HCID 131717513, Verbindung

HRID 1885316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885316
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)=[O:6].[F:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[OH2:6].[ClH:1].[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[ClH:1]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2737266(4-Fluorophenyl)(piperidin-1-yl)methanoneHCID 10263700HCID 10263700, Verbindung

Produkt 1

HCID 131717513HCID 131717513, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of N-(2-chloroethyl)-1,2-benzisothiazole-3-carboxamide (3.5 g) and 1-(4-fluorobenzoyl)piperidine (3.63 g) in dry 1-methyl-2-pyrrolidinone (125 ml) was heated with stirring to 180° C., under nitrogen. After 3 hr, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium carbonate solution. The aqueous phase was extracted with ethyl acetate, and the combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was triturated with ether, and the filtrate was concentrated. The residue was chromatographed on silica using ethyl acetate as the eluent. The appropriate fractions were combined and concentrated. The residue was taken up in ether and hydrogen chloride in ether was added. The precipitate was recrystallized from methanol/dichloromethane/ether to provide 1.21 g (18.1%) of product, mp 188°-190° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was triturated with ether
  9. concentrationthe filtrate was concentrated
  10. customThe residue was chromatographed on silica
  11. concentrationconcentrated
  12. additionhydrogen chloride in ether was added
  13. customThe precipitate was recrystallized from methanol/dichloromethane/ether

Quellen und Nachweise

ORD-Eintrag
ord-2df9d57137dd44eab1c9230f2d870c32
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143923

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