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

HRID 2268767Notes

Reaction equation

HRID 2268767 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 hr and then more potassium hydroxide (40 g) was added and the reaction mixture heated under reflux for a further 4 hr. The reaction mixture was allowed to cool to room temperature and poured onto ice-water (3 l) and stirred for 1 hr and the precipitated solid isolated by filtration and dried at 50° C. in vacuo to give a solid. (WO 9747302).

Workup

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

Sources & evidence

ORD record
ord-743f7b713943464383d9a9e462b7e90e
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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