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

HRID 224359Notes

Reaction equation

HRID 224359 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Cl.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:16]3[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 766596-Methoxy-1H-indoleHCID 30848514-Piperidone hydrochloride

Product 1

HCID 130190056-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 g of 6-methoxy-1H-indole, 41.75 g of the hydrate of 4-piperidone hydrochloride and 205 ml of 2 N methanolic potassium hydroxide solution was refluxed under an inert atmosphere for 81/2 hours and the mixture was slowly diluted with water to a volume of 1.2 liters. Crystallization began and the mixture was stirred for 30 minutes and then was filtered. The recovered product was rinsed with water and dried at 50° C. under reduced pressure over a desiccant to obtain 23.05 g of 6-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole.

Workup

  1. temperaturewas refluxed under an inert atmosphere for 81/2 hours
  2. customCrystallization
  3. filtrationwas filtered
  4. washThe recovered product was rinsed with water
  5. customdried at 50° C. under reduced pressure over a desiccant

Sources & evidence

ORD record
ord-addc605bf10149f296cef468ad00de0f
Source dataset
uspto-grants-1980_11
Patent number
US04232031

Reaction notes

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