Piperidine → 3-(4-methoxybenzylidene)-oxindole

HRID 1600878Notes

Reaction equation

HRID 1600878 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].[CH:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.N1CCCCC1>C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 321710Oxindole

Product 1

HCID 28031093-(4-methoxybenzylidene)-oxindoleYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g of oxindole was dissolved in 40 ml of ethanol, and 2.0 g of p-anisaldehyde was added thereto at room temperature. Subsequently, 1.5 ml of piperidine was added, and the mixture was refluxed with heat for 13 hours. After completion of reaction, the reaction mixture was cooled. Crystals that precipitated were collected by filtration. The resultant crude product was washed with methanol, to thereby obtain 2.6 g (yield 71%) of the title compound in the form of yellow crystals. The melting point and elementary analysis data are shown in Table 13, and NMR and MS spectrum data are shown in Table 14.

Workup

  1. customat room temperature
  2. temperaturethe mixture was refluxed
  3. temperaturewith heat for 13 hours
  4. customAfter completion of reaction
  5. temperaturethe reaction mixture was cooled
  6. customCrystals that precipitated
  7. filtrationwere collected by filtration
  8. washThe resultant crude product was washed with methanol

Sources & evidence

ORD record
ord-7bb46894e1654296b284ecce26c6fed7
Source dataset
uspto-grants-1999_11
Patent number
US05977130

Reaction notes

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