Hydrochloric Acid → HCID 69947315, compound

Participants

Reaction Conditions

Reaction Steps

207 mg of 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-[4-phenyl-1,2,3,6-tetrahydro-1-pyridyl]-1-propanone hydrochloride was dissolved in a solvent mixture comprising 10 ml of ethanol and 10 ml of tetrahydrofuran. After ice-cooling to 0° C., 319 mg of sodium boron hydride was added thereto in portions for 7 hours. After decomposing the sodium boron hydride by adding conc. hydrochloric acid, the solvent was removed by evaporation. Then the residue was neutralized by adding an aqueous solution of sodium hydroxide and extracted 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 was dissolved in 7 ml of tetrahydrofuran. Then 250 mg of tosic acid monohydrate was added and the mixture was heated under reflux for 60 minutes. After evaporating the solvent, the residue was neutralized by adding an aqueous solution of sodium hydroxide and extracted with ethyl acetate. 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 purified by silica gel column chromatography (chloroform:methanol=100:1-3). Then the product was converted into hydrochloride by adding 0.3 ml of a 1N hydrochloric acid/ethanol solution and recrystallized from methanol/ethyl acetate. Thus 47 mg of the title compound was obtained in the form of a pale yellow solid product.

Provenance & Evidence