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

HRID 481944Notes

Reaction equation

HRID 481944 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 27637245-Bromo-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2a7c1d3fc64c498d851b1bde5483dac0
Source dataset
uspto-grants-1998_08
Patent number
US05792760

Reaction notes

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