Piperidine → 1-(4,5-Dihydro-2-thiazolyl)-1,3-dihydro-3-[(4-methoxyphenyl)methylene]-2H-indol-2-one

HRID 1414863Notes

Reaction equation

HRID 1414863 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.N1CCCCC1>C1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[CH:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[C:7]1=[O:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 214055041-(4,5-Dihydro-1,3-thiazol-2-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 542215681-(4,5-Dihydro-2-thiazolyl)-1,3-dihydro-3-[(4-methoxyphenyl)methylene]-2H-indol-2-oneYield 53.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a warmed benzene solution of 1-(2-thiazolin-2-yl)-indolin-2-one (2.0 g, 7.2 mmol) and p-methoxybenzaldehyde (1.5 g, 11 mmole) is added piperidine (0.6 ml). The mixture is heated at reflux temperature for 2 hours. The reaction mixture is then washed with NaHSO3 solution, diluted HCl and water. The organic phase is dried over anhydrous MgSO4 and concentrated in vacuo. The residue is recrystallized once each from acetone/hexane, acetonitrile and CHCl3 /methanol and gives 1.3 g (43%) of the product (m.p. 164.5°-167° C, softens at 149° C).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. washThe reaction mixture is then washed with NaHSO3 solution, diluted HCl and water
  4. dry with materialThe organic phase is dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized once each from acetone/hexane, acetonitrile and CHCl3 /methanol

Sources & evidence

ORD record
ord-7c70a85204d147cb9a766fd1cb41b33f
Source dataset
uspto-grants-1977_01
Patent number
US04002749

Reaction notes

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