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

HRID 583063Notes

Reaction equation

HRID 583063 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO>[F:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH:16]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 3512786-FluoroindoleHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Powdered potassium hydroxide (144.4 g) was added carefully to a mechanically stirred mixture of 6-fluoroindole (49.23 g, 0.364 mol) and 4-piperidone monohydrate (111.93 g, 0.728 mol) in methanol (1500 ml). The mixture was then heated under reflux under nitrogen for 18 hours and then more potassium hydroxide (40 g) was added and the reaction mixture heated under reflux for a further 4 hours. The reaction mixture was allowed to cool to room temperature and poured onto ice-water (3000 ml) and stirred for 1 hour and the precipitated solid isolated by filtration and dried at 50° C. in vacuo to give a solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux under nitrogen for 18 hours
  3. temperaturethe reaction mixture heated
  4. temperatureunder reflux for a further 4 hours
  5. additionpoured onto ice-water (3000 ml)
  6. customthe precipitated solid isolated by filtration
  7. customdried at 50° C. in vacuo
  8. customto give a solid

Sources & evidence

ORD record
ord-be80ee73b12a47e0a1bbaa7850f2a575
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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