Potassium Hydroxide → 5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

HRID 843752Notes

Reaction equation

HRID 843752 reaction equation
[OH-].[K+].[CH3:3][N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1.[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2>CO.O>[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[C:7]1[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH:8]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 249055-BromoindoleHCID 740491-Methyl-4-piperidone

Product 1

HCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 56.11 gm (306 mMol) potassium hydroxide in 300 mL methanol were added 38 mL (306 mMol) 1-methyl-4-piperidone followed by 30.0 gm (153 mMol) 5-bromo-1H-indole. The reaction mixture was stirred at reflux for 18 hours. The reaction mixture was then cooled to ambient and diluted with 1.5 L water. The resultant white solid was filtered, washed sequentially with water and diethyl ether, and then dried under vacuum to give 44.6 gm (100%) 5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was then cooled to ambient and
  3. filtrationThe resultant white solid was filtered
  4. washwashed sequentially with water and diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7bcfe2c390ce451794cd15293bf3faab
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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