5-Methoxyindole → 5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

HRID 224361Notes

Reaction equation

HRID 224361 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.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:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:16]1[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=1

Participants

5

Reactant 3

HCID 138725-MethoxyindoleHCID 14797Potassium HydroxideHCID 30848514-Piperidone hydrochloride

Product 1

HCID 1080295-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 14.7 g of 5-methoxy-1H-indole, 30.7 g of the monohydrate of 4-piperidone hydrochloride and 150 ml of 2 N methanolic potassium hydroxide solution was refluxed under an inert atmosphere for 81/2 hours and was then cooled. 300 ml of water were added to the mixture which caused crystallization and the mixture was cooled to 10° C. and filtered. The recovered product was empasted 3 times with water, twice with ethanol and twice with ether. The product was dried at 20° C. under reduced pressure to obtain 18.25 g of 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in the form of a clear yellow powder melting at 183° C.

Workup

  1. temperaturewas refluxed under an inert atmosphere for 81/2 hours
  2. temperaturewas then cooled
  3. customcrystallization
  4. filtrationfiltered
  5. customThe product was dried at 20° C. under reduced pressure

Sources & evidence

ORD record
ord-c0d59215554649048149fba22bf42dda
Source dataset
uspto-grants-1980_11
Patent number
US04232031

Reaction notes

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