4-Piperidone → 5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1936636Notes

Reaction equation

HRID 1936636 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[NH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.O.Cl>CO>[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH:14]=1

Participants

6

Reactant 4

HCID 337214-PiperidoneHCID 678615-FluoroindoleHCID 5360545SodiumHCID 21885828Hydrate;hydrochloride

Product 1

HCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium (60 g , 2.6 mol) in 1000 ml of methanol was added 5-fluoroindole (49 g, 0.36 mol) and 4-piperidone.H2O.HCl (170 g, 1.11 mol). The mixture was heated under reflux for 18 h, then concentrated , water was added and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and then concentrated. The resulting solid was dissolved in methanol (about 200 ml) and then diluted with water (about 1000-1500 ml). The precipitate was collected , washed with water and petroleum ether and then dried in a vacuum oven at 60° C. Yield 74 g (95%) of a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 h
  3. concentrationconcentrated
  4. additionwater was added
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe resulting solid was dissolved in methanol (about 200 ml)
  9. additiondiluted with water (about 1000-1500 ml)
  10. customThe precipitate was collected
  11. washwashed with water and petroleum ether
  12. customdried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-d90cc4e2a08e414db975b97e4d180d19
Source dataset
uspto-grants-2002_05
Patent number
US06391896B1

Reaction notes

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