Formaldehyde → HCID 22097376, compound

HRID 1458996Notes

Reaction equation

HRID 1458996 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]=1[CH3:9])(=[O:3])[CH3:2].[ClH:16].[CH2:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:30]=O>C(O)C>[ClH:16].[CH3:9][C:8]1[N:7]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:6]=[CH:5][C:4]=1[C:1](=[O:3])[CH2:2][CH2:30][N:27]1[CH2:28][CH2:29][N:24]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 27566531-Benzylpiperazine hydrochloride2×HCID 154563751-(2-Pyrimidinyl)-4-acetyl-5-methylpyrazole

Product 1

HCID 22097376HCID 22097376, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.01 g of 4-acetyl-1-(2-pyrimidinyl)-5-methylpyrazole was dissolved in 80 ml of anhydrous ethanol. After adding 1.25 g of 1-benzylpiperazine hydrochloride and 0.45 g of paraformaldehyde, the mixture was heated under reflux for 18 hours. Further, 0.60 g of 1-benzylpiperazine hydrochloride and 0.20 g of paraformaldehyde were added and the resulting mixture was heated under reflux for additional 8 hours. After cooling, the crystals were collected by filtration and extracted with chloroform and a saturated aqueous solution of sodium hydrogencarbonate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue thus obtained was purified by silica gel column chromatography (50 g, chloroform:methanol=50:1), converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution and then recrystallized from ethanol. Thus 742 mg of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for additional 8 hours
  5. temperatureAfter cooling
  6. filtrationthe crystals were collected by filtration
  7. extractionextracted with chloroform
  8. washThe extract was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customAfter evaporating the solvent
  11. customthe residue thus obtained
  12. customwas purified by silica gel column chromatography (50 g, chloroform:methanol=50:1)
  13. additionby adding a 1N hydrochloric acid/ethanol solution
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ba04bfafee154d15b26707097ac3c703
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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