Piperidine → 5-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357105Notes

Reaction equation

HRID 357105 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])[C:5]=12.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH2:30]O)[CH:23]=1.N1CCCCC1>C(O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][CH:30]=[C:18]2[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6]3[C:5]4[N:4]([CH:3]=[CH:2][N:1]=4)[CH:9]=[CH:8][CH:7]=3)[C:19]2=[O:20])[CH:23]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 178613-PyridinepropanolHCID 189368403-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Product 1

HCID 572830815-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.53 g (5.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 676 mg (5.0 mmol) of 3-(3-pyridyl)-1-propanol in 20 ml of ethanol, 43 mg (0.5 mmol) of piperidine was added, followed by refluxing for 3.5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=50/1→25/1) to yield 0.49 g (23.0%, yellow oily substance) of the desired product.

Workup

  1. temperatureby refluxing for 3.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with purified water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, chloroform/methanol=50/1→25/1)

Sources & evidence

ORD record
ord-c947573615af4313a4b48bc6bf39459a
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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