Ethanol → HCID 22097359, compound

HRID 1458984Notes

Reaction equation

HRID 1458984 reaction equation
Cl.[CH3:2][C:3]1[N:7]([C:8]2[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=2)[N:6]=[CH:5][C:4]=1[C:16](=O)[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:21][CH2:20]1.C(O)C.B.[Na].Cl.C(O)C>O1CCCC1>[ClH:31].[CH3:2][C:3]1[N:7]([C:8]2[N:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[N:13]=2)[N:6]=[CH:5][C:4]=1/[CH:16]=[CH:17]/[CH2:18][N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 702EthanolHCID 21887872Ethanol hydrochlorideHCID 22097315HCID 22097315, compoundHCID 178418435HCID 178418435, compound2×

Product 1

HCID 22097359HCID 22097359, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.0 g of 1-[5-methyl-1-(4,6-dimethyl-2-pyrimidinyl)-4-pyrazolyl]-3-[4-(3,4-dichlorophenyl)-1-piperazinyl]-1-propanone hydrochloride was dissolved in a solvent mixture comprising 50 ml of ethanol and 50 ml of tetrahydrofuran. After cooling with ice to 0° C., 500 mg of sodium boron hydride was added and the mixture was stirred at the same temperature for 45 minutes. Further, 50 mg of sodium boron hydride was added and the mixture was stirred for additional 2 hours. Then it was neutralized by adding a 1N hydrochloric acid/ethanol solution. After evaporating the ethanol, chloroform was added to the concentrated residue. Then it was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, 50 ml of dioxane, 50 ml of tetrahydrofuran and 220 mg of p-toluenesulfonic acid monohydrate were added to the obtained residue. Then the resulting mixture was heated under reflux for 5 hours. After evaporating the solvent, chloroform was added to the residue. Then it was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (chloroform:methanol=30:1), converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution and recrystallized from ethanol to thereby give 560 mg of the title compound.

Workup

  1. stirringthe mixture was stirred for additional 2 hours
  2. customAfter evaporating the ethanol, chloroform
  3. additionwas added to the concentrated residue
  4. washThen it was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  6. customAfter evaporating the solvent, 50 ml of dioxane, 50 ml of tetrahydrofuran and 220 mg of p-toluenesulfonic acid monohydrate
  7. additionwere added to the obtained residue
  8. temperatureThen the resulting mixture was heated
  9. temperatureunder reflux for 5 hours
  10. customAfter evaporating the solvent, chloroform
  11. additionwas added to the residue
  12. washThen it was washed with a saturated aqueous solution of sodium hydrogencarbonate
  13. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  14. customAfter evaporating the solvent
  15. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)
  16. additionby adding a 1N hydrochloric acid/ethanol solution
  17. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1104b4223a274616922237a30df80f0c
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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