Ethanol → HCID 22097359, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence