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Industrially Scalable Synthesis of Anti-alzheimer Drug Donepezil
Corresponding Author(s) : Santosh L. Gaonkar
Asian Journal of Chemistry,
Vol. 29 No. 9 (2017): Vol 29 Issue 9
Abstract
This paper describes a simple, efficient and industrially scalable total synthesis of donepezil hydrochloride. The article also reported the X-ray studies of the 2-(1-benzylpiperidin-4-ylmethyliden)-5,6-dimethoxyindan-1-one, an intermediate in the synthesis of donepezil. The crystal structure analysis of 2-(1-benzylpiperidin-4-ylmethyliden)-5,6-dimethoxyindan-1-one shows that it crystallizes in monoclinic class under the space group P121/c1 with cell parameters, a = 17.2992(7) Å, b = 10.1999(4) Å, c = 11.9539(5) Å, b = 103.450(2)°, V = 2051.42(15) Å3 and Z = 4.
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- L. Bertram and R.E. Tanzi, Nat. Rev. Neurosci., 9, 768 (2008); https://doi.org/10.1038/nrn2494.
- R.S. Shah, H.G. Lee, Z. Xiongwei, G. Perry, M.A. Smith and R.J. Castellani, Biomed. Pharmacother., 62, 199 (2008); https://doi.org/10.1016/j.biopha.2008.02.005.
- G.L. Wenk, J. Clin. Psychiatry, 64 Suppl. 9, 7 (2003).
- E.L. Barner and S.L. Gray, Ann. Pharmacother., 32, 70 (1998); https://doi.org/10.1345/aph.17150.
- S.H. Ferris, Clin. Ther., 23, 3 (2001); https://doi.org/10.1016/S0149-2918(01)80162-4.
- E. Giacobini, Neurochem. Res., 28, 515 (2003); https://doi.org/10.1023/A:1022869222652.
- H. Sugimoto, Y. Yamanish, Y. Iimura and Y. Kawakami, Curr. Med. Chem., 7, 303 (2000); https://doi.org/10.2174/0929867003375191.
- H. Sugimoto, Chem. Rec., 1, 63 (2001); h t t p s : / / d o i . o rg/10.1002/1528-0691(2001)1:1<63::AIDTCR9>3.0.CO;2-J.
- G. Benzi and A. Moretti, Eur. J. Pharmacol., 346, 1 (1998); https://doi.org/10.1016/S0014-2999(98)00093-4.
- J. Grutzendler and J.C. Morris, Drugs, 61, 41 (2001); https://doi.org/10.2165/00003495-200161010-00005.
- H. Sugimoto, H. Ogura, Y. Arai, Y. Iimura and Y. Yamanishi, Jpn. J. Pharmacol., 89, 7 (2002); https://doi.org/10.1254/jjp.89.7.
- S.L. Gaonkar, K.M.L. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006); https://doi.org/10.1016/j.ejmech.2006.03.002.
- S.L. Gaonkar and H. Shimizu, Tetrahedron, 66, 3314 (2010); https://doi.org/10.1016/j.tet.2010.03.006.
- N. Bhandari and S.L. Gaonkar, Chem. Heterocycl. Comp., 51, 320 (2015); https://doi.org/10.1007/s10593-015-1701-x.
- B. Namratha, D. Bilehal, V. Shyam Kumar and S.L. Gaonkar, Res. Chem. Intermed., 42, 1885 (2016); https://doi.org/10.1007/s11164-015-2123-1.
- B.S. Priya, S. Nanjunda Swamy, M.V. Tejesvi, Basappa, G. Sarala, S.L. Gaonkar, S. Naveen, J. Shashidhara Prasad and K.S. Rangappa, Eur. J. Med. Chem., 41, 1262 (2006); https://doi.org/10.1016/j.ejmech.2006.05.011.
- Bruker APEX2 and SAINT, Bruker AXS Inc. Madison, Wisconsin (2004).
- G.M. Sheldrick, SHELXS-97, University of Gottingen, Germany, (1997).
References
L. Bertram and R.E. Tanzi, Nat. Rev. Neurosci., 9, 768 (2008); https://doi.org/10.1038/nrn2494.
R.S. Shah, H.G. Lee, Z. Xiongwei, G. Perry, M.A. Smith and R.J. Castellani, Biomed. Pharmacother., 62, 199 (2008); https://doi.org/10.1016/j.biopha.2008.02.005.
G.L. Wenk, J. Clin. Psychiatry, 64 Suppl. 9, 7 (2003).
E.L. Barner and S.L. Gray, Ann. Pharmacother., 32, 70 (1998); https://doi.org/10.1345/aph.17150.
S.H. Ferris, Clin. Ther., 23, 3 (2001); https://doi.org/10.1016/S0149-2918(01)80162-4.
E. Giacobini, Neurochem. Res., 28, 515 (2003); https://doi.org/10.1023/A:1022869222652.
H. Sugimoto, Y. Yamanish, Y. Iimura and Y. Kawakami, Curr. Med. Chem., 7, 303 (2000); https://doi.org/10.2174/0929867003375191.
H. Sugimoto, Chem. Rec., 1, 63 (2001); h t t p s : / / d o i . o rg/10.1002/1528-0691(2001)1:1<63::AIDTCR9>3.0.CO;2-J.
G. Benzi and A. Moretti, Eur. J. Pharmacol., 346, 1 (1998); https://doi.org/10.1016/S0014-2999(98)00093-4.
J. Grutzendler and J.C. Morris, Drugs, 61, 41 (2001); https://doi.org/10.2165/00003495-200161010-00005.
H. Sugimoto, H. Ogura, Y. Arai, Y. Iimura and Y. Yamanishi, Jpn. J. Pharmacol., 89, 7 (2002); https://doi.org/10.1254/jjp.89.7.
S.L. Gaonkar, K.M.L. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006); https://doi.org/10.1016/j.ejmech.2006.03.002.
S.L. Gaonkar and H. Shimizu, Tetrahedron, 66, 3314 (2010); https://doi.org/10.1016/j.tet.2010.03.006.
N. Bhandari and S.L. Gaonkar, Chem. Heterocycl. Comp., 51, 320 (2015); https://doi.org/10.1007/s10593-015-1701-x.
B. Namratha, D. Bilehal, V. Shyam Kumar and S.L. Gaonkar, Res. Chem. Intermed., 42, 1885 (2016); https://doi.org/10.1007/s11164-015-2123-1.
B.S. Priya, S. Nanjunda Swamy, M.V. Tejesvi, Basappa, G. Sarala, S.L. Gaonkar, S. Naveen, J. Shashidhara Prasad and K.S. Rangappa, Eur. J. Med. Chem., 41, 1262 (2006); https://doi.org/10.1016/j.ejmech.2006.05.011.
Bruker APEX2 and SAINT, Bruker AXS Inc. Madison, Wisconsin (2004).
G.M. Sheldrick, SHELXS-97, University of Gottingen, Germany, (1997).