Ethanol → HCID 18545390, compound

HRID 564858Notes

Reaction equation

HRID 564858 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]=1[CH3:9])(=[O:3])[CH3:2].Cl.[Cl:17][C:18]1[CH:19]=[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:21]=[C:22]([Cl:24])[CH:23]=1.[CH2:31](O)C>>[ClH:17].[Cl:24][C:22]1[CH:21]=[C:20]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:2][C:1]([C:4]3[CH:5]=[N:6][N:7]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=4)[C:8]=3[CH3:9])=[O:3])[CH2:27][CH2:26]2)[CH:19]=[C:18]([Cl:17])[CH:23]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 28055541-[5-methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]ethan-1-oneHCID 13059027HCID 13059027, compound

Product 1

HCID 18545390HCID 18545390, compound

Procedure

In 150 ml of absolute ethanol was dissolved 2.26 g of 4-acetyl-1-(2-pyridyl)-5-methylpyrazole, and 2.94 g of 1-(3,5-dichlorophenyl)piperazine hydrochloride and 0.9 g of p-formaldehyde were added to the solution, followed by refluxing for 6 hours. To the reaction mixture was further added 0.40 g of p-formaldehyde, and the refluxing was continued for an additional 24 hour period. About a half of the ethanol was removed by evaporation, and the precipitate was collected by filtration. The precipitate was dissolved in chloroform, washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was subjected to column chromatography on silica gel using a mixture of chloroform-methanol (50:1 by volume) as a developing solvent. The fraction containing the desired compound was concentrated. A 1N hydrochloric acid/ethanol solution was added to the residue, followed by concentration. The residue was recrystallized from ethanol to yield 2.90 g of the title compound.

Workup

  1. additionwere added to the solution
  2. temperatureby refluxing for 6 hours
  3. customAbout a half of the ethanol was removed by evaporation
  4. filtrationthe precipitate was collected by filtration
  5. dissolutionThe precipitate was dissolved in chloroform
  6. washwashed successively with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation
  9. additiona mixture of chloroform-methanol (50:1 by volume) as a developing solvent
  10. additionThe fraction containing the desired compound
  11. concentrationwas concentrated
  12. additionA 1N hydrochloric acid/ethanol solution was added to the residue
  13. concentrationfollowed by concentration
  14. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b66f88fdd8f34f5caf305d9fe0df5da6
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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