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Green Synthesis of 3-(2-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-yl) ethyl-6,7,8,9-tetrahydro-9-hydroxy-2-methylpyridol[1,2-a]pyrimidin-4-one
Corresponding Author(s) : D. Vivekananda Reddy
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
Paliperidone has been synthesized in high yields by condensation of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahy-dropyridol[1,2a]pyrimidin-4-one (1) and (2,4-difluoro-phenyl)-piperidin-4-yl-methanone oxime (2) using K2CO3 as a base, refluxing in acetonitrile for 16 h. The novel intermediate (3) underwent internal cyclization in PEG-600 as solvent yielded paliperidone (4). Paliperidone (4) from novel intermediate (3) has also been prepared under microwave condition using PEG-600 and also in presence of a base KOH in toluene at 70 °C for 3 h in higher yields.
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- P. Revill, N. Serradell and J. Bolós, Drugs Future, 31, 579 (2006); doi:10.1358/dof.2006.031.07.1008562.
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- Basappa, K. Mantelingu, M.P. Sadashiva and K.S. Rangappa, Indian J. Chem., 43B, 1954 (2004.
- J.R. Vascuri, M. Kagga and B. Gupta, N.A. Vekariya and A. Islam, Der Pharm. Lett., 3, 240 (2011).
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References
P. Revill, N. Serradell and J. Bolós, Drugs Future, 31, 579 (2006); doi:10.1358/dof.2006.031.07.1008562.
G. Mannens, M.L. Huang, W. Meuldermans, J. Hendrickx, R. Woestenborghs and J. Heykants, Drug Metab. Dispos., 21, 1134 (1993).
S. Bellino, P. Bozzatello, C. Rinaldi and F. Bogetto, Depress. Res. Treat., Article ID 680194 (2011).
M. Vermeir, I. Naessens, B. Remmerie, G. Mannens, J. Hendrickx, P. Sterkens, K. Talluri, S. Boom, M. Eerdekens, N. van Osselaer and A. Cleton, Drug Metab. Dispos., 36, 769 (2008); doi:10.1124/dmd.107.018275.
(a) Chem. Abstr., 123, 340172c (1995); (b) Chem. Abstr., 153, 37181 (2010); (c) C.G.M. Janssen, A.G. Knaeps, L.E.J. Kennis and J. Vandenberk, U.S. Patent 5158952 B1 (1992).
Basappa, K. Mantelingu, M.P. Sadashiva and K.S. Rangappa, Indian J. Chem., 43B, 1954 (2004.
J.R. Vascuri, M. Kagga and B. Gupta, N.A. Vekariya and A. Islam, Der Pharm. Lett., 3, 240 (2011).
Y.K. Chang, N.D. Kim, G.S. Lee, J.H. Lee and M.S. Lee, WO Patent 2004035573 A1 (2004).