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

HRID 367369Notes

Reaction equation

HRID 367369 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.N1CCCC1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH:14]=1

Participants

5

Reactant 3

HCID 249055-BromoindoleHCID 31268PyrrolidineHCID 740491-Methyl-4-piperidone

Product 1

HCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-1H-indole (4.31 g, 22 mmol), 1-methyl-4-piperidone (2.46 mL, 20 mmol) and pyrrolidine (17 mL, 200 mmol) were mixed in ethanol (30 mL) and refluxed for 72 hours. The mixture was cooled to room temperature and the resulting solid, collected by filtration, washed with methanol and dried to provide the title compound as a white solid (4.40 g, 76%). mp>230° C., dec.

Workup

  1. temperaturerefluxed for 72 hours
  2. filtrationthe resulting solid, collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-b7cd3a6acffc4baeb09b2ac3fbb58cd8
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Reaction notes

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