Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
An Improved Scalable Process for Synthesis of Piperidin-4-yl-carbamates
Corresponding Author(s) : Sitaramaiah Devarasetty
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
An efficient route for the synthesis of methyl piperidine-4-yl-carbamate para-toluene sulfonate salt has been developed. The synthesis involves the reductive amination of 1-benzylpiperidin-4-one with ammonia using Raney-Ni as a catalyst followed by de-protection of benzyl group and finally by making its salt. The advantage of this methodology includes use of easily available commercial raw materials and shorter reaction times with high yields makes this process most viable for large scale manufacturing methyl piperidine-4-yl-carbamate salts.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- K.W. Woods, C. Lai, J.M. Miyashiro, Y. Tong, A.S. Florjancic, E.K. Han, N. Soni, Y. Shi, L. Lasko, J.D. Leverson, E.F. Johnson, A.R. Shoemaker and T.D. Penning, Bioorg. Med. Chem. Lett., 22, 1940 (2012); https://doi.org/10.1016/j.bmcl.2012.01.041.
- S. Yoshinobu and A. Satoshi, Pyrazolothiazole Compound and Medication, PCT Int. Appl. 2016035814 (2016).
- C.-M. Andersson, N. Schlienger, A. Fejzic, E. Hansen and J. Pawlas, N-Substituted Piperidine Derivatives as Serotonin Receptor Agents, US Patent 20060094758 (2006).
- D. Mukherjee, S. Shirase, K. Mashima and J. Okuda, Angew. Chem. Int. Ed., 55, 13326 (2016); https://doi.org/10.1002/anie.201605236.
- L. Martinez-Montero, A. Díaz-Rodríguez, V. Gotor, V. Gotor-Fernández and I. Lavandera, Green Chem., 17, 2794 (2015); https://doi.org/10.1039/C5GC00525F.
- I. Huber, I. Zupkó, I.J. Kovács, R. Minorics, G. Gulyás-Fekete, G. Maász and P. Perjési, Monatsh. Chem., 146, 973 (2015); https://doi.org/10.1007/s00706-015-1426-7.
- Y. Sasano, N. Kogure, T. Nishiyama, S. Nagasawa and Y. Iwabuchi, Chem. Asian J., 10, 1004 (2015); https://doi.org/10.1002/asia.201403245.
- Y. Sasano, S. Nagasawa, M. Yamazaki, M. Shibuya, J. Park and Y. Iwabuchi, Angew. Chem. Int. Ed., 53, 3236 (2014); https://doi.org/10.1002/anie.201309634.
- C.W. Sun, H.F. Wang, J. Zhu, D.R. Yang, J. Xing and J. Jin, J. Heterocycl. Chem., 50, 1374 (2013); https://doi.org/10.1002/jhet.916.
- D.S. Rawat, B. Wang, N. Kumar, S. Manohar, X. Yang, G. Sun and N. Ni, Curcumin Analogs and Methods of Making and using Thereof, US Patent 14418025 (2015).
- N. Kumar, G. Sun, N. Ni, W. Chen, A.D.C. Molina, B. Wang and S.D. Rawat, Chem. Biol. Interact., 3, 164 (2013);
- Z. Yuyao, Faming Zhuanli Shenqing, 102731369 (2012).
- J. Zhongliang, Huaxue Shijie, 45, 484 (2004).
- Y.P. Yuan, S.B. Wang, G.H. Gong and Z.S. Quan, Lett. Drug Des. Discov., 11, 1070 (2014); https://doi.org/10.2174/1570180811666140623204022.
- T. Liu, B. Huang, Y. Tian, X. Liang, H. Liu, H. Liu, P. Zhan, E. De Clercq, C. Pannecouque and X. Liu, Chem. Biol. Drug Des., 86, 107 (2015); https://doi.org/10.1111/cbdd.12468.
- A. Feula and J.S. Fossey, RSC Advances, 3, 5370 (2013); https://doi.org/10.1039/c3ra40228b.
- Y. Zhang, B. Liu, T. Yu, X. Zhang, S. Zhang, J. Zhang and C. Cheng, Heteroaromatic Derivatives and Pharmaceutical Applications Thereof, PCT Int. Appl., 2016034134 (2016).
- Y.L. Li, A.P. Combs, E.W. Yue and H.Y. Li, Substituted Fused Aryl and Heteroaryl Derivatives as pi3k Inhibitors, PCT Int. Appl., 2011075630 (2011).
References
K.W. Woods, C. Lai, J.M. Miyashiro, Y. Tong, A.S. Florjancic, E.K. Han, N. Soni, Y. Shi, L. Lasko, J.D. Leverson, E.F. Johnson, A.R. Shoemaker and T.D. Penning, Bioorg. Med. Chem. Lett., 22, 1940 (2012); https://doi.org/10.1016/j.bmcl.2012.01.041.
S. Yoshinobu and A. Satoshi, Pyrazolothiazole Compound and Medication, PCT Int. Appl. 2016035814 (2016).
C.-M. Andersson, N. Schlienger, A. Fejzic, E. Hansen and J. Pawlas, N-Substituted Piperidine Derivatives as Serotonin Receptor Agents, US Patent 20060094758 (2006).
D. Mukherjee, S. Shirase, K. Mashima and J. Okuda, Angew. Chem. Int. Ed., 55, 13326 (2016); https://doi.org/10.1002/anie.201605236.
L. Martinez-Montero, A. Díaz-Rodríguez, V. Gotor, V. Gotor-Fernández and I. Lavandera, Green Chem., 17, 2794 (2015); https://doi.org/10.1039/C5GC00525F.
I. Huber, I. Zupkó, I.J. Kovács, R. Minorics, G. Gulyás-Fekete, G. Maász and P. Perjési, Monatsh. Chem., 146, 973 (2015); https://doi.org/10.1007/s00706-015-1426-7.
Y. Sasano, N. Kogure, T. Nishiyama, S. Nagasawa and Y. Iwabuchi, Chem. Asian J., 10, 1004 (2015); https://doi.org/10.1002/asia.201403245.
Y. Sasano, S. Nagasawa, M. Yamazaki, M. Shibuya, J. Park and Y. Iwabuchi, Angew. Chem. Int. Ed., 53, 3236 (2014); https://doi.org/10.1002/anie.201309634.
C.W. Sun, H.F. Wang, J. Zhu, D.R. Yang, J. Xing and J. Jin, J. Heterocycl. Chem., 50, 1374 (2013); https://doi.org/10.1002/jhet.916.
D.S. Rawat, B. Wang, N. Kumar, S. Manohar, X. Yang, G. Sun and N. Ni, Curcumin Analogs and Methods of Making and using Thereof, US Patent 14418025 (2015).
N. Kumar, G. Sun, N. Ni, W. Chen, A.D.C. Molina, B. Wang and S.D. Rawat, Chem. Biol. Interact., 3, 164 (2013);
Z. Yuyao, Faming Zhuanli Shenqing, 102731369 (2012).
J. Zhongliang, Huaxue Shijie, 45, 484 (2004).
Y.P. Yuan, S.B. Wang, G.H. Gong and Z.S. Quan, Lett. Drug Des. Discov., 11, 1070 (2014); https://doi.org/10.2174/1570180811666140623204022.
T. Liu, B. Huang, Y. Tian, X. Liang, H. Liu, H. Liu, P. Zhan, E. De Clercq, C. Pannecouque and X. Liu, Chem. Biol. Drug Des., 86, 107 (2015); https://doi.org/10.1111/cbdd.12468.
A. Feula and J.S. Fossey, RSC Advances, 3, 5370 (2013); https://doi.org/10.1039/c3ra40228b.
Y. Zhang, B. Liu, T. Yu, X. Zhang, S. Zhang, J. Zhang and C. Cheng, Heteroaromatic Derivatives and Pharmaceutical Applications Thereof, PCT Int. Appl., 2016034134 (2016).
Y.L. Li, A.P. Combs, E.W. Yue and H.Y. Li, Substituted Fused Aryl and Heteroaryl Derivatives as pi3k Inhibitors, PCT Int. Appl., 2011075630 (2011).