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Synthesis 2015; 47(10): 1387-1389
DOI: 10.1055/s-0034-1380505
DOI: 10.1055/s-0034-1380505
psp
A New and Practical Synthesis of Vortioxetine Hydrobromide
Further Information
Publication History
Received: 25 January 2015
Accepted after revision: 05 March 2015
Publication Date:
13 April 2015 (online)
Abstract
A new and improved synthetic route to vortioxetine hydrobromide is established on a hectogram scale through three simple steps in 63% yield and with 99% purity (HPLC). The key step is the cyclization of the piperazine ring in the final step. Purification methods for the intermediates involved in the route are given.
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References
- 1 Y. M. and L. J. have contributed equally to this work.
- 2 Gibb A, Deeks ED. Drugs 2014; 74: 135
- 3 du Jardin KG, Jensen JB, Sanchez C, Pehrson AL. Eur. Neuropsychopharmacol. 2014; 24: 160
- 4 Mahableshwarkar AR, Jacobsen PL, Chen Y. Curr. Med. Res. Opin. 2013; 29: 217
- 5a Ruhland T, Smith GP, Bang-Andersen B, Pueschl A, Moltzen EK, Andersen K. WO 2003,029,232, 2003
- 5b Ruhland T, Christensen KL. WO 2014,128,207, 2014
- 6 Bang-Andersen B, Ruhland T, Jorgensen M, Smith G, Frederiksen K, Jensen KG, Zhong H, Nielsen SM, Hogg S, Mork A, Stensbol TB. J. Med. Chem. 2011; 54: 3206
- 7 Christensen KL. WO 2013,102,573, 2013
- 8a Liu KG, Robichaud AJ. Tetrahedron Lett. 2005; 46: 7921
- 8b Juvale K, Wiese M. Bioorg. Med. Chem. Lett. 2012; 22: 6766
- 8c Zupancic B. WO 2014,161,976, 2014
- 9 Li H, Cao Z, Xiao H. Med. Chem. Res. 2008; 16: 28
- 10a Pennell AM. K, Aggen JB, Wright JJ. K, Sen S, Mcmaster BE, Dairaghi DJ, Chen W, Zhang P. WO 2005,056,015, 2005
- 10b Pennell AM. K, Aggen JB, Wright JJ. K, Sen S, Mcmaster BE, Dairaghi DJ. US 2004,0162,282, 2004
- 11 Sun A, Moore TW, Gunther JR, Kim MS, Rhoden E, Du Y, Fu H, Snyder JP, Katzenellenbogen JA. ChemMedChem 2011; 6: 654
- 12 Novi M, Garbarino G, Petrillo G, Dell’Erba C. J. Chem. Soc., Perkin Trans. 2 1987; 623
- 13 Nicolajsen HV, de Diego LH, Rock MH. WO 2010,094,285, 2010