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

HRID 1276333Notes

Reaction equation

HRID 1276333 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][CH2:17][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 18403962HCID 18403962, compound

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 piperidine monohydrate (111.93 g, 0.728 mol) in methanol (1500 ml) The mixture was then heated under reflux under nitrogen for 18 h and then more potassium hydroxide (40 g) was added and the reaction mixture heated under reflux for a further 4 h. The reaction mixture was allowed to cool to room temperature and poured onto ice-water (3000 ml) and stirred for 1 h and the precipitated solid isolated by filtration and dried at 50C in vacuo to give a solid.

Workup

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

Sources & evidence

ORD record
ord-fb499f71d178474b945019ae5a9360c5
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

Loading…