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

HRID 2382112Notes

Reaction equation

HRID 2382112 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.Cl.O.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[OH-].[K+].O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:16]1[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 678615-FluoroindoleHCID 2723901Piperonylamine

Product 1

HCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-fluoroindole (6.65 g, 49.2 mmol) and 4-piperidone hydrate hydrochloride (18.9 g, 123 mmol) in methanol solution of 2 N KOH (90 mL) is refluxed for 6 h. After cooling to rt, water (150 mL) is added and stirred at rt for 30 minutes. The resulting precipitate is filtered, washed with water (10 mL) and ether (15 mL), and dried in vacuo to afford 5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-indole (6.34 g, 60%). MS: 217 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.40 (br, H), 7.57 (dd, H), 7.24-7.37 (m, H), 7.23 (s, H), 6.98 (t, H), 6.20 (s, H), 3.62 (m, 2H), 3.16 (m, 2H), 2.50 (s, 2H).

Workup

  1. temperatureis refluxed for 6 h
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water (10 mL) and ether (15 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ae8d2d46ed574a45a387ea7d9783f6d4
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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