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

HRID 1003543Notes

Reaction equation

HRID 1003543 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-16dc04b9d4d642b0beab3ae2317b5bcc
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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