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Citation: Zhang Huaiyuan, Tang Rongping, Wu Jiawei, Hu Yulai. A Novel Synthetic Method for Flibanserin[J]. Chemistry, ;2018, 81(11): 1048-1051. shu

A Novel Synthetic Method for Flibanserin

1.
Lan Zhou Petrochemical Polytechnic Lanzhou 730060
2.
Northwest Normal University Lanzhou 730070

Received Date: 28 June 2018
Accepted Date: 16 August 2018

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A novel and efficient synthesis of flibanserin was reported. One pot reaction of benzaldehyde, N-phenyl hydroxylamine and trimethylsilyl cyanide promoted by diacetoxyiodobenzene was used to construct benzimidazolones, which is the key skeleton structure of flibanserin. Subsequently, it is reacted with 1, 2-dibromoethane to generate compound 8, which hydrolyzed in concentrated hydrochloric acid to produce intermediate 9. At last, intermediate 9 was reacted with 10 to obtain flibanserin with a total yield of 29%. The structure of all compounds was characterized by ¹H NMR, ¹³C NMR and HRMS. This method has the advantages of inexpensive raw material, little byproduct and moderate yield.
- Flibanserin,
- Diacetoxyiodobenzene,
- Benzimidazolones,
- Synthesis
1. [1]
  E D Deeks. Drugs, 2015, 75(15): 1815~1822.
2. [2]
  I Dhanuka, J A Simon. Expert Opin. Pharmaco., 2015, 16(16): 2523~2529.
3. [3]
  L Jaspers, F Feys, W M Bramer et al. JAMA Inter. Med., 2016,176(4): 453~462.
4. [4]
  F Borsini, K Evans, K Jason et al. CNS Drug Rev., 2002, 8(2): 117~142.
5. [5]
  E Jolly, A Clayton, J Thorp et al. Sexologies, 2008, 17(Suppl 1): S133~S134.
6. [6]
  A Mullard. Nat. Rev. Drug Discov., 2015, 14,669.
7. [7]
  G Bietti, F Borsini, M Turconi et al. US: 5576318.
8. [8]
  D Mohan Rao, P Krishna Reddy, B Venkat Reddy. WO: 2012156983A1.
9. [9]
  G Vernin, H Domlog, C Siv et al. J. Heterocycl. Chem., 1981, 18(1): 85~89.
10. [10]
  F Yang, C Wu, Z Li et al. Org. Proc. Res. Dev., 2016, 20(9): 1576~1580.
11. [11]
  D A Evans, H J Song, K R Fandrick. Org. Lett., 2006, 8(15): 3351~3354.
1. [1]
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2. [2]
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