Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis Memantine and Memantine Hydrochloride by Direct Amination of 1-Bromo-3,5-dimethyladamantane with Thiourea

Author(s): Thi Hong Tham Nguyen, Binh Duong Vu*, Dinh Chau Phan*, Thi Hong Thanh Nguyen, Quang Anh Luong and Thi Xuan Thu Ngo

Volume 20, Issue 7, 2023

Published on: 16 February, 2023

Page: [672 - 677] Pages: 6

DOI: 10.2174/1570178620666230123094019

Price: $65

Abstract

Memantine hydrochloride (MH) is a first-line therapeutic drug approved by the US FDA for the management of moderate to severe Alzheimer's disease. This study involves the synthesis of memantine hydrochloride from 1-bromo-3,5-dimethyladamantane through a reaction with thiourea. The research results showed that the solvent reaction was propylene glycol (PG); the total time reaction was 5.5 hours, the temperature reaction in the first stage was 160°C and in the second stage was 80°C; the overall yield was 82.44%. The reaction intermediates were confirmed by the IR, MS,1HNMR, and 13C-NMR spectra.

« Previous Next »
Graphical Abstract

[1]
Shukla, S. WO Patent 1,222,38A1, 2006.
[2]
Madhra, M.K.; Sharma, M.; Khanduri, C.H. Org. Process Res. Dev., 2007, 11(5), 922-923.
[http://dx.doi.org/10.1021/op700138p]
[3]
Reddy, J.M.; Prasad, G.; Raju, V.; Ravikumar, M.; Himabindu, V.; Reddy, G.M. Org. Process Res. Dev., 2007, 11(2), 268-269.
[http://dx.doi.org/10.1021/op060246+]
[4]
Tyagi, O.P.; Ramanjaneyulu, G.S.; Mohan, B.; Kumar, I.V.S.; Rao, K.N.A. WO Patent 1,324,76A2, 2007.
[5]
Roy, R.U.; Chand, P.; Kumar, R.; Dhar, D.S. . Patent WO 062472 A2,, 2008.
[6]
Vigano, E.; Landonio, E.; Lanfranconi, S.; Molteni, R. Patent US 0258885A1, 2006.
[7]
Gold, M.R.; Koller, H.; Pyerin, M. US Patent 8,796,491 B2, 2014.
[8]
Ivleva, E.A.; Klimochkin, Y.N. Org. Prep. Proced. Int., 2017, 49(2), 155-162.
[http://dx.doi.org/10.1080/00304948.2017.1291004]
[9]
Ponnaiah, R.; Prasad, A.; Rana, P.M.; Kanzariya, K.S.; Dolia, M.B. WO Patent 067,252 A1, 2010.
[10]
Vu, B.D.; Ho, B.N.M.; Tran, V.H.; Phan, D.C. Org. Prep. Proced. Int., 2020, 52(5), 463-467.
[http://dx.doi.org/10.1080/00304948.2020.1785807]
[11]
Vu, B.D.; Ho Ba, N.M.; Pham, V.H.; Phan, D.C. ACS Omega, 2020, 5(26), 16085-16088.
[http://dx.doi.org/10.1021/acsomega.0c01589] [PMID: 32656430]
[12]
Sugawara, K.; Endo, M.; Taguchi, Y.; Kushibe, K. JP Patent, 039, 656A, 2017.
[13]
Leonova, M.V.; Skomorokhov, M.Y.; Moiseev, I.K.; Klimochkin, Y.N. Russ. J. Org. Chem., 2015, 51(12), 1703-1709.
[http://dx.doi.org/10.1134/S1070428015120064]
[14]
Nguyen, T.H.T.; Nguyen, T.D.; Phan, D.C.; Vu, B.D. Int. J. Pharm. Sci. Res., 2021, 12(12), 6370-6383.
[15]
Nguyen, T.H.T.; Le, V.D.; Ngo, S.T.; Nguyen, T.H.T.; Phan, D.C.; Vu, B.D. Asian J. Chem., 2022, 34(2), 251-255.
[http://dx.doi.org/10.14233/ajchem.2022.23447]
[16]
Schickaneder, C.P. US Patent 20090082596 A1, 2009.
[17]
Kilaru, S.; Periyandi, N.; Thennati, R. WO Patent 062,724 A2,, 2005.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy