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

HRID 641865Notes

Reaction equation

HRID 641865 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO>[Br: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][N:14]([CH3:13])[CH2:15][CH:16]=1

Participants

5

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 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of KOH (6.7 g, 118.45 mmol) in methanol (60 mL) was added to 5-bromo-1H-indole (10 g, 50.51 mmol) in a 250 mL 3-necked round bottom flask. 1-methylpiperidin-4-one (7.7 g, 67.46 mmol) was then added dropwise with stirring, while cooling to a temperature of 20° C. The resulting solution was allowed to react, with stirring, for 4 hours while the temperature was maintained at 73° C. The reaction mixture was then cooled to 15° C. and filtered. The filter cake was washed with water (3×50 mL). The product was purified by recrystallization from ethanol to afford 12.3 g (83%) of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole as a white solid.

Workup

  1. customto react
  2. stirringwith stirring, for 4 hours while the temperature
  3. temperaturewas maintained at 73° C
  4. temperatureThe reaction mixture was then cooled to 15° C.
  5. filtrationfiltered
  6. washThe filter cake was washed with water (3×50 mL)
  7. customThe product was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-20878434b11b4095a1b268f6c617458e
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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