3-Chloropropionyl chloride → 9-(3-Chloropropionyl)-1,2,3,4,4a,9a-hexahydrocarbazole

HRID 2395261

Reaktionsgleichung

Reaktionsgleichung von HRID 2395261
[CH2:1]1[CH:13]2[CH:5]([C:6]3[C:11]([NH:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1.[Cl:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>CC(C)=O>[Cl:14][CH2:15][CH2:16][C:17]([N:12]1[CH:13]2[CH:5]([CH2:4][CH2:3][CH2:2][CH2:1]2)[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:18]

Komponenten

4

Edukt 2

HCID 693643-Chloropropionyl chlorideHCID 1011622,3,4,4a,9,9a-Hexahydro-1H-carbazole

Produkt 1

HCID 189716109-(3-Chloropropionyl)-1,2,3,4,4a,9a-hexahydrocarbazoleAusbeute 111,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of 10 g 1,2,3,4,4a,9a-hexahydro carbazole in 30 ml acetone was added a solution of 8.3 g 3-chloropropionyl chloride in 30 ml acetone dropwise at ambient temperature and the mixture was refluxed for 1 hour. The solvent was then distilled off under reduced pressure and the residue was dissolved in 100 ml of dichloromethane and washed with 10% hydrochloric acid twice. The solution was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to provide about 17 g of 9-(3-chloro-propionyl)-1,2,3,4,4a,9a-hexahydrocarbazole as a viscous oil. This oil was not purified but submitted directly to the next reaction.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. distillationThe solvent was then distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 100 ml of dichloromethane
  4. washwashed with 10% hydrochloric acid twice
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-faa17e0ad4c74af58268b7c9b76f9222
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05814642

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