Reaktion #364086

Reaktionsgleichung

2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

potassium carbonate

ethyl acetate

1-Benzyl-4-methyl-4-phenylpiperidine

→

title compound

Ausbeute 53.0%

2a-[4-(4-Methyl-4-phenyl-piperidyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Ausbeute 53.0%

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction solution was filtered
2. 2
   Sonstigethe solvent was evaporated from the resulting mother liquor under a reduced pressure
3. 3
   workup.DISSOLUTIONthe thus obtained material was dissolved in anhydrous N,N-dimethylformamide (2 ml)
4. 4
   workup.STIRRINGthe mixture was stirred at 60° C. for 3 hours
5. 5
   Extraktionthe reaction product was extracted with ethyl acetate
6. 6
   Waschenwashed with saturated brine
7. 7
   Trocknendried with anhydrous sodium sulfate
8. 8
   SonstigeThen the compound obtained by the evaporation of the solvent under a reduced pressure
9. 9
   Sonstigewas separated
10. 10
    Sonstigepurified by a silica gel column chromatography

Vorschrift

1-Benzyl-4-methyl-4-phenylpiperidine (62 mg, 0.24 mmol) was dissolved in ethanol (2 ml). Thereto was added palladium-carbon (10 mg), and the resulting solution was stirred at a room temperature for 17 hours in an atmosphere of argon. The reaction solution was filtered, the solvent was evaporated from the resulting mother liquor under a reduced pressure, and the thus obtained material was dissolved in anhydrous N,N-dimethylformamide (2 ml). The resulting solution was mixed with 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (79 mg, 0.26 mmol) and potassium carbonate (51mg, 0.37mmol) and then the mixture was stirred at 60° C. for 3 hours. The reaction solution was mixed with ethyl acetate and water, and the reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 50 mg of the title compound (0.12 mmol, 53% in yield).

Quelle