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

HRID 725956Notes

Reaction equation

HRID 725956 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-35fa2f9330484f6b9f191270dba933fd
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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