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

HRID 2357493Notes

Reaction equation

HRID 2357493 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Cl.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.O>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:17]1[CH2:18][CH2:19][NH:14][CH2:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 871105-ChloroindoleHCID 30848514-Piperidone hydrochloride

Product 1

HCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

KOH (8.19 g, 146 mmole), 5-chloroindole (5.0 g, 33 mmole) and piperidine-4-one hydrochloride (10.22 g, 85.7 mmole) were suspended in methanol (50 ml) and heated for 8 hours at 65° C. under argon. Water (50 ml) was added dropwise at RT to the mixture over a period of 40 minutes. The solid thereby formed was filtered off, washed with water (3×20 ml) and recrystallised from methanol (20 ml). 5-chloro-3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole was obtained in a yield of 6.4 g (90%) as a yellow solid with an m.p. of 166°-168° C.

Workup

  1. customThe solid thereby formed
  2. filtrationwas filtered off
  3. washwashed with water (3×20 ml)
  4. customrecrystallised from methanol (20 ml)

Sources & evidence

ORD record
ord-9a482033b2d34400a1ce16d36ed45b96
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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