Water → HCID 22097367, compound

HRID 1458976Notes

Reaction equation

HRID 1458976 reaction equation
Cl.[CH3:2][C:3]1[N:7]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:6]=[CH:5][C:4]=1[C:14](=O)[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH2:19][CH2:18]1.B.[Na].O>CO>[ClH:29].[CH3:2][C:3]1[N:7]([C:8]2[N:9]=[CH:10][CH:11]=[CH:12][N:13]=2)[N:6]=[CH:5][C:4]=1/[CH:14]=[CH:15]/[CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 22097375HCID 22097375, compoundHCID 178418435HCID 178418435, compound2×

Product 1

HCID 22097367HCID 22097367, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.7 g of 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-[4-(2-chlorophenyl)-1-piperazinyl]-1-propanone hydrochloride was dissolved in 300 ml of methanol. After adding 1.25 g of sodium boron hydride, the obtained mixture was stirred at room temperature for 2 hours. To the reaction mixture was further added 0.6 g of sodium boron hydride followed by stirring for 2 hours. Under ice cooling, water was added to the reaction mixture and the methanol was removed by evaporation. The residue was extracted with chloroform and the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to silica gel column chromatography and developed with a solvent mixture (chloroform/methanol, 30:1) to thereby give 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-[4-(2-chlorophenyl-)1-piperazinyl]-1-propanol. Next, 16 ml of a 1N hydrochloric acid/ethanol solution was added to the product. After dissolving by heating, ether was further added thereto. The crystals thus precipitated were collected by filtration to thereby give 1.26 g of the title compound.

Workup

  1. stirringby stirring for 2 hours
  2. customthe methanol was removed by evaporation
  3. extractionThe residue was extracted with chloroform
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporating the solvent
  7. additionNext, 16 ml of a 1N hydrochloric acid/ethanol solution was added to the product
  8. dissolutionAfter dissolving
  9. temperatureby heating
  10. additionether was further added
  11. customThe crystals thus precipitated
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2acb981142754c24b5461fc53c860fc8
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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