Methylhydrazine → 3-(3-(4-(4chlorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1-methyl-1H-indazole

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Reaction Steps

This compound could be also obtained by the following method. That is, 4-(4-chlorophenyl)-1-(4-oxo-4-(2-oxocyclohexyl)butyryl)piperazine obtained by using 4-oxo4-(2-oxocyclohexyl)-n-butyric acid and 1-(4-chlorophenyl)piperazine instead of 3-(4,5,6,7-tetrahydro-2H-indazol-3-yl)propionic acid and 4-(4-chlorophenyl)piperidine used in Example 102 was refluxed under heating in a methanol solvent with methyl hydrazine. After the completion of the reaction, the solvent was evaporated under reduced pressure to give an oily substance. This compound was dissolved in tetrahydrofuran and thereto was added lithium aluminum hydride in an ice bath. After the completion of the reaction, a mixture of tetrahydrofuran—water was added, and then ethyl acetate and magnesium sulfate were further added. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 3-(3-(4-(4chlorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1-methyl-1H-indazole.

Provenance & Evidence