Piperidine → (Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

HRID 352291

Reaction equation

HRID 352291 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[NH:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.N1CCCCC1>CO>[NH:11]1[CH:15]=[CH:14][CH:13]=[C:12]1/[CH:16]=[C:3]1\[C:2](=[O:10])[NH:1][C:9]2[C:4]\1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 13854Pyrrole-2-carboxaldehydeHCID 321710Oxindole

Product 1

HCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-oneYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of oxindole (137 mg, 1.03 mmol), pyrrole-2-carboxaldehyde (115.1 mg, 1.21 mmol) and piperidine (40 μL, 0.404 mmol) in 2.0 mL MeOH was heated at reflux for 3 h. The mixture was cooled in an ice bath and the solid which formed was collected by filtration to give the title compounds (208 mg, 96%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was cooled in an ice bath
  4. customthe solid which formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4933e8f1efb841dd8e9a6093d4e561b7
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Linked notes

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