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

HRID 397616Notes

Reaction equation

HRID 397616 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[OH-].[K+]>CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3[CH2:15][CH2:16][NH:11][CH2:12][CH:13]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 337214-PiperidoneHCID 3512786-Fluoroindole

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-fluoroindole (2 g, 15 mmol) and 4-piperidone (3 g, 19.6 mmol) in 2 N solution of KOH in MeOH (60 mL) was stirred at reflux for 72 h. The mixture was concentrated to ¼ volume, diluted with H20 and filtered affording 2.5 g (77%) as a pale yellow solid: mp 202-204° C.; MS (APCI) m/z 217 [M+H]+.

Workup

  1. temperatureat reflux for 72 h
  2. concentrationThe mixture was concentrated
  3. additiondiluted with H20
  4. filtrationfiltered
  5. customaffording 2.5 g (77%) as a pale yellow solid

Sources & evidence

ORD record
ord-220836493af94b11ad7e9d570f8a52ea
Source dataset
uspto-grants-2003_08
Patent number
US06610712B2

Reaction notes

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