Piperidine → 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one

HRID 47241Notes

Reaction equation

HRID 47241 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[C:13]1[CH:17]=[C:16](C)[NH:15][C:14]=1[CH:19]=O.N1CCCCC1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:19][C:14]1[NH:15][CH:16]=[CH:17][CH:13]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1528015-ChlorooxindoleHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 404857155-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-oneYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 μL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h. The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40%) as a red/orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-76849b10a0ea4e5e82b4c6fdc1dc3cc2
Source dataset
uspto-grants-2004_03
Patent number
US06699863B1

Reaction notes

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