Formaldehyde → 1-[5-Methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-[4-(4-methoxyphenyl)-1-piperazinyl]-1-propanone hydrochloride

HRID 1458994Notes

Reaction equation

HRID 1458994 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[C:11]([CH3:12])=[C:10]([C:13](=[O:15])[CH3:14])[CH:9]=[N:8]1.[ClH:16].Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[CH2:32]=O>C(O)C>[ClH:16].[CH3:12][C:11]1[N:7]([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[N:8]=[CH:9][C:10]=1[C:13](=[O:15])[CH2:14][CH2:32][N:29]1[CH2:30][CH2:31][N:26]([C:23]2[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 154563751-(2-Pyrimidinyl)-4-acetyl-5-methylpyrazole

Product 1

HCID 220973491-[5-Methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-[4-(4-methoxyphenyl)-1-piperazinyl]-1-propanone hydrochlorideYield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g of 1-(2-pyrimidinyl)-4-acetyl-5-methyl-pyrazole was dissolved in 50 ml of ethanol. After adding 1.3 g of 1-(4-methoxyphenyl)piperazine dihydrochloride and 0.8 g of paraformaldehyde, the mixture was heated under reflux for 24 hours. Further, 0.8 g of paraformaldehyde was added and the resulting mixture was heated under reflux for additional 48 hours. Then the reaction mixture was concentrated and neutralized by adding a saturated aqueous solution of sodium hydrogencarbonate. After extracting with chloroform, 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 (chloroform:methanol=50:1), converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution and then recrystallized from ethanol. Thus 1.1 g of the title compound was obtained in the form of a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for additional 48 hours
  5. concentrationThen the reaction mixture was concentrated
  6. additionby adding a saturated aqueous solution of sodium hydrogencarbonate
  7. extractionAfter extracting 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 (chloroform:methanol=50:1)
  13. additionby adding a 1N hydrochloric acid/ethanol solution
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-39f0cf642faa4ca886bedab29feed32b
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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