Potassium Hydroxide → 7-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1779627Notes

Reaction equation

HRID 1779627 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.O.Cl.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1>CO.O>[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[C:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH:17]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1046447-chloro-1H-indoleHCID 2723901Piperonylamine

Product 1

HCID 185458497-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (6.89 g, 0.12 mol) was dissolved in methanol (30 mL). To the solution were added 7-chloroindole (4.65 g, 0.031 mol), 4-piperidone hydrochloride hydrate (9.48 g, 0.061 mol). The mixture was stirred at reflux temperature under nitrogen for about a day, and was cooled and diluted with 50 mL of water, added dropwise. The solid was collected, washed with water and vacuum dried. Yield 5.6 g (78%) as a yellow solid. mp 197°-201° C. FDMS m/e=232 (M+).

Workup

  1. temperatureat reflux temperature under nitrogen for about a day
  2. temperaturewas cooled
  3. additionadded dropwise
  4. customThe solid was collected
  5. washwashed with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-7afbf90ee5094395b97ab173aff6b728
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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