| Summary: | 碩士 === 高雄醫學大學 === 藥學研究所碩士在職專班 === 93 === Methyl 3-piperidinylpropionate, the key intermediate for the preparation of pridinol and diphenidol, was efficiently prepared from piperidine and methyl acrylate without using any catalyst, and solvent. Furthermore, when methyl 3-piperidinylpropionate was reacted with 2 equivalent of phenyl magnesium bromide produced pridinol, which was used in clinics as a muscle relaxant, in good yields. The giving pridinol was converted into various salts by treatment with corresponding acids, such as HCl, maleic acid, succinic acid, respectively. The relative thermal stability of each pridinol salt was determined by DSC.
On the other hand, methyl 3-piperidinylpropionate, which can be reduced efficiently by NaBH4 in THF-MeOH system in stead of using traditional reducing agent, LiAlH4, was easily converted into N-3-chloropropylpiperidine by thionyl chloride. The resulting chloride was reacted with magnesium to produce corresponding Grignard reagent which was allowed to react with benzophenone to give the desired diphenidol in good yields. The giving diphenidol was converted into various salts by treatment with corresponding acids, such as HCl, maleic acid, succinic acid, L-tartaric acid, citric acid, and malonic acid, respectively. The relative thermal stability of each diphenidol salt will be determined by DSC.
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