Butanal → HCID 57132710, compound

HRID 357041Notes

Reaction equation

HRID 357041 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]3[C:18](=[O:19])[CH2:17][S:16][C:15]3=[O:20])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:21](=O)[CH2:22][CH2:23][CH3:24].N1CCCCC1>C(O)C>[CH:21](=[C:17]1[S:16][C:15](=[O:20])[N:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)[C:18]1=[O:19])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 18936698HCID 18936698, compound

Product 1

HCID 57132710HCID 57132710, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.00 g (3.46 mmol) of 3-[4-(imidazo-[1,2-a]pyridin-5-yl)butyl]thiazolidine-2,4-dione and 0.31 ml (3.46 mmol) of n-butyraldehyde in 25 ml of ethanol, 0.03 ml (0.35 mmol) of piperidine was added, followed by refluxing for 2 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate→ethyl acetate/ethanol=10/1) to yield 1.08 g (90.8%, light yellow oily substance) of the desired product.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, ethyl acetate→ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-63a431bb9442407a9f38220d78829dc5
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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