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

HRID 1456968Notes

Reaction equation

HRID 1456968 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO>[F:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH:16]=1)=[CH:7][NH:8]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 27745024-Fluoroindole

Product 1

HCID 102202224-fluoro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.18 gm (21.0 mMol) potassium hydroxide in 10 mL methanol were added 1.00 gm (7.4 mMol) 4-fluoro-1H-indole and 1.82 mL (14.8 mMol) 1-methyl-4-piperidone. The reaction mixture was stirred for 28 hours at reflux and then was allowed to cool. The crystals which formed were filtered, washed with methanol and dried under vacuum at 60° C. to give 1.17 gm (69%) of the title compound.

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. customThe crystals which formed
  4. filtrationwere filtered
  5. washwashed with methanol
  6. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-a4ac61242964432abdd99008e2b23ea5
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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