Scale-Up Synthesis of Antidepressant Drug Vilazodone

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• 作者：Bin Hu ; Qiao Song ; Yungen Xu
• 刊名：Organic Process Research & Development
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：16
• 期：9
• 页码：1552-1557
• 全文大小：255K
• 年卷期：v.16,no.9(September 21, 2012)
• ISSN：1520-586X

文摘

A scale-up synthesis of antidepressant drug vilazodone was accomplished in five steps. Friedel鈥揅rafts acylation of 1-tosyl-1H-indole-5-carbonitrile with 4-chlorobutyryl chloride, selective deoxygenation in NaBH₄/CF₃COOH system coupled with ethyl 5-(piperazin-1-yl)-benzofuran-2-carboxylate hydrochloride, one-step deprotection and esterolysis, and the final ammonolysis led to the target molecule vilazodone in 52.4% overall yield and 99.7% purity. This convenient and economical procedure is remarkably applicable for scale-up production.