3,5-Dichlorobenzenesulfonyl chloride → 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole

HRID 1006417

Reaktionsgleichung

Reaktionsgleichung von HRID 1006417
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[C:28]([Cl:30])[CH:29]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+].O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:31]([C:26]2[CH:25]=[C:24]([Cl:23])[CH:29]=[C:28]([Cl:30])[CH:27]=2)(=[O:33])=[O:32])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 27285324-(4-Benzyl-piperazin-1-yl)-1H-indole

Produkt 1

HCID 121371244-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indoleAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4-(4-Benzyl-piperazin-1-yl)-1H-indole (274 mg, 0.94 mmole) and 50 mg tetra-n-butylammonium hydrogen sulfate was stirred in a mixture of 10 mL toluene and 5 mL 4 N sodium hydroxide. Solid 3,5-dichlorobenzenesulfonyl chloride (246 mg, 1.0 mmole) was added in one portion. The reaction mixture was stirred at room temperature for 6 hours, then it was diluted with 20 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 10 mL saturated sodium chloride solution, dried (magnesium sulfate) and concentrated. Recrystallization from dichloromethane provided 473 mg of 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole, m.p. 201-203° C.

Aufarbeitung

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 10 mL saturated sodium chloride solution
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customRecrystallization from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9c0ec165595848a990ab93ee514ccaec
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790848B2

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