Potassium Hydroxide → 5-Bromo-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 481944

Reaktionsgleichung

Reaktionsgleichung von HRID 481944
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.Cl.O>CO.O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:16]1[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 249055-BromoindoleHCID 337214-PiperidoneHCID 21885828Hydrate;hydrochloride

Produkt 1

HCID 27637245-Bromo-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4.29 gm (77 mmol) potassium hydroxide in 50 ml methanol were added 5.0 gm (26 mmol) 5-bromoindole and 7.84 gm (51 mmol) 4piperidone .HCl.H2O and the reaction mixture was stirred for 18 hours at reflux under a nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, diluted with 500 ml water and the mixture extracted well with dichloromethane. The combined organic extracts were washed with water followed by saturated aqueous sodium chloride and dried over sodium sulfate. The remaining organics were concentrated under reduced pressure to give 6.23 gm (86.5%) of the title compound as a yellow oil.

Aufarbeitung

  1. temperatureat reflux under a nitrogen atmosphere
  2. extractionthe mixture extracted well with dichloromethane
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationThe remaining organics were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2a7c1d3fc64c498d851b1bde5483dac0
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792760

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