A novel and practical asymmetric synthesis of dapoxetine hydrochloride

Yijun Zhu1, Zhenren Liu2, Hongyan Li2

  • 1State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, China; School of Pharmacy, Fudan University, No. 826, Zhangheng Rd., Shanghai 201203, China.

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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