Piperazine → 5-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indole

HRID 1793869

Reaktionsgleichung

Reaktionsgleichung von HRID 1793869
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O.O>[F:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:12]=[CH:13]2

Komponenten

5

Edukt 2

HCID 4837PiperazineHCID 222201261-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole

Produkt 1

HCID 99985735-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indoleAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole (0.210 g, 0.7 mmole) and anhydrous piperazine (0.3 g, 3.4 mmole) in dimethylsulfoxide (3.0 mL) was heated at 100° in a sealed tube for 16 h. The reaction mixture was diluted with 15 mL water and extracted with 20 mL ethyl acetate. The organic phase was washed with three 10 mL portions of water, 10 mL saturated sodium chloride, dried (magnesium sulfate), and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to provide the 5-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indole (0.123 g), m.p. 77–78°.

Aufarbeitung

  1. extractionextracted with 20 mL ethyl acetate
  2. washThe organic phase was washed with three 10 mL portions of water, 10 mL saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-149316315f5344be8e5c9550c7eb59e8
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022708B2

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