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

HRID 726407Notes

Reaction equation

HRID 726407 reaction equation
[OH-].[K+].[F: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>[F: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 337214-PiperidoneHCID 678615-FluoroindoleHCID 21885828Hydrate;hydrochloride

Product 1

HCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 74 gm potassium hydroxide in 673 mL methanol were added 10.0 gm (74 mMol) 5-fluoroindole and 23.3 gm (151 mMol) 4-piperidone.HCl.H2O. The reaction mixture was stirred at reflux for 18 hours. The reaction mixture was diluted with 1.3 L of water and the resulting precipitate recovered by filtration and dried under reduced pressure to give 10.75 gm (67.2%) of 5-fluoro-3-[1,2,5,6-tetrahydro-4-pyridyl]-1H-indole as a yellow solid.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationthe resulting precipitate recovered by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-8bd99eb98c93411d9a055f2de79a1f54
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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