• 作者： 徐聖煦; 賴春蓮; 巫月梅; 陳琴心
• 作者服務機構： 國立清華大學化學系
• 中文摘要： 吩坦尼（Fentanyl）可以從苯乙胺與丙烯酸甲酯以三個階段予以製成。第一階段為苯乙胺與
  丙烯酸甲酯以1：2摩爾比加成，此加成物（Ⅰ）用甲醇鈉行 Dieckmann 化縮合，再用鹽酸水
  解，脫羧而得 1-苯乙基-4-?啶酮（Ⅱ），產率為66%；第二階段將Ⅱ與苯胺縮合脫水，成為
  亞胺，然後用乙醇，鈉還原，得1-苯乙基-4-苯胺基?啶（Ⅲ），產率為67%；第三階段將Ⅲ
  與丙酸酐行醯化反應，製得吩坦尼，產率為93%。整個製備的總產率為41%，故這個製備方法
  已適合工業上分批式生產的要求。
• 英文摘要： Fentanyl can be prepared from phenethyl-amine and methyl acrylate by successive threesteps. In the first step, a series of reactions wasincluded. Phenethylamine was reacted withmethyl acrylate to form an 1:2 adduct (Ⅰ)This I was reacted with sodium methoxide toform a Dieckmann condensation product. Hy-drolysis and decarboxylation of above Dieck-mann consensation product, 1-phenethyl-4-piperidone (Ⅱ) was produced in 66% yield. In the second step, Ⅱ was condensed withaniline in the presense of catalytic amount ofρ-toluenesulfonic acid to give an imine deriva-tive, which was reduced by metallic sodium inethanol to give 1-phenethyl-4-anilinopiperidine(Ⅲ) in 67% yield. The third step was the propionation ofⅢ with propionic anhydride. Fentanyl wasproduced in 93% yield. The overall yield of these three steps was41%. This three steps process can be applied asbatch process for the industrial preparation ofFentanyl.
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