Catalytic hydrogenation in the process of 2-((1-benzylpiperidin-4-yl) methyl)-5,6-dimethoxy-2,3-dihydroinden-1-one hydrochloride synthesis I. Catalyst screening and finding the optimal reaction conditions

• Authors: Zrinka Mastelic Samardzic , Stanka Zrncevic
• Languages of publication: EN

Abstracts

EN

Catalytic hydrogenation of 2-((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methylene)-5,6-dimethoxy-2,3-dihydroinden- 1-one hydrochloride () to 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydroinden- 1-one hydrochloride (2) was investigated in the batch-slurry reactor. The 5% Pt/C catalyst was chosen to search the optimal reaction conditions because of its higher catalytic activity compared to other catalysts used in the work. To investigate the catalyst activity, selectivity and stability, the effect of agitation speed, catalyst loading, solvent, temperature, hydrogen pressure and catalyst reuse were studied.The initial rate of hydrogenation increases with the increase of catalyst loading, with the temperature and solvent polarity, if alcohols were used as solvents. The hydrogenation rate decreases with higher hydrogen pressure and that was explained by competitive adsorption of both reactants.The results also indicate that 5% Pt/C is a promising catalyst for 1 hydrogenation because at relatively mild reaction conditions selectivity towards main product was high (98%) and catalyst maintains its activity during successive runs.

Keywords

EN

catalytic hydrogenation; catalyst screening; catalyst selectivity; optimal reaction conditions.

• Publisher: De Gruyter Open
• Journal: Polish Journal of Chemical Technology
• Year: 2012
• Volume: 14
• Issue: 3
• Pages: 38-47

Dates

published

1 - 10 - 2012

received

accepted

online

31 - 10 - 2012

Contributors

author

Zrinka Mastelic Samardzic

• R & D, Chemistry, PLIVA Croatia Ltd. Prilaz Baruna Filipovica 25, Zagreb, Croatia

author

Stanka Zrncevic

• University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, Croatia

References

• 1. The American Society of Health- System Pharmacists, AHFS® Consumer Medication Information. ©Copyright, 2010. http://www.ncbi.nlm.nih.gov/pubmedhealth/?term=donepezil.
• 2. Gutman, A.L., Shokolnik, E., Tishin, B., Nisnevich, G. & Zaltzman, I. (2002). U.S. Patent No. 6,492,522. Washington, D.C.: U.S. Patent and Trademark Offi ce.
• 3. Lerman, O., Kaspi, J., Arad, O., Alnabari, M. & Sery. Y. (2004). U.S. Patent No. 6,844,440. Washington, D.C.: U.S. Patent and Trademark Offi ce.
• 4. Reddy, M.S., Eswaraiah, S., Thippannachar, M.V., Chandrashekar, E.R.R., Kumar, P.A.,Kumar, K.N. (2001). U.S. Patent No. 7,148,354. Washington, D.C.: U.S. Patent and Trademark Offi ce.
• 5. Iimura, Y. (2001), U.S. Patent No. 6,252,081. Washington, D.C.: U.S. Patent and Trademark Offi ce.
• 6. Yatendra, K., Mohan, P., Asok, N. & Nitin, M. WO Patent No. 2004082685(A1). World Intellectual property organization.
• 7. Sugimoto, H., Ogura, H., Arai,Y., Limura, Y., Yamanishi, Y. (2002). Research and development of donepezil hydro-chloride, a new type of acetylcholinesterase inhibitor, Jap. J.Pharmacology. 89, 7-20.
• 8. Niphade, N., Mali, A., Jagtap, K., Ojha, R.C., Vankawala, P.J. & Mathad, V.T. (2008). Org. Process Res. Dev. 12 (4), 731-735. DOI/10.1021/op800066m.[Crossref]
• 9. Attanti, S. & Yadla, V. WO Patent No. /2008/010235. World Intellectual property organization.
• 10. Ashvin, K., Aggarwal, C., Vankatesran, S. & Lalit, W. US Patent No. 20100113793, Washington, D.C.: U.S. Patent and Trademark Offi ce.
• 11. Thippannachar, M.V., Chintaman, N.N., Jayndal, V.P. & Chaturlal, M.A. Indian Patent Application no. 1073/MUM/2008.
• 12. Reichardt, C. (1990). Solvents and Solvent Effects inOrganic Chemistry; VCH: Weinheim,
• 13. Rajadhyaksha, R.A. & Karwa, S.L. (1986). Solvents effects in catalytic hydrogenation. Chem.Eng.Sci. 41, 1765. DOI: 10.1016/0009-2509(86)87055-5.[Crossref]
• 14. McClellan, A.L. (1963). Tables of Experimental DipoleMoments, Vol. I; Freeman and Co., San Francisco, DOI: 10.1002/ange.19650770627.[Crossref]
• 15. Singh, U.K. & Vanice, M.A. (2001). Kinetics of liquid-phase hydrogenation reaction over supported metal catalysts. Appl.Catal. A: Gen. 213, 1-24. DOI: 10.1016/S0926-860X(00)00885-1.[Crossref]
• 16. Cerveny, L. & Ruzicka, V.; Catal. Rev.-Sci.Eng. 1982, 24, 503-566.
• 17. Bakker, J.J.W., Van der Neut, A.G., Kreutzer, M.T., Moulijin, J.A. & Kapteijn, F. (2010). Catalyst performance changes induced by palladium phase transformation in the hydrogenation of benzonitrile. J. Catal. 274, 176-191. DOI: 10.1016/j.cat.2010.06.013.[WoS][Crossref]
• 18. Bernas, H., Taskinen, A., Wärnå, J. & Murzin, Y. (2009). Hydrogenolysis of hydroxymatairesinol on a Pd/C catalyst. J. Mol. Catal. A: Chem. 306, 33-39, DOI: 10.1016/j. molcata.2009.02.015.[Crossref]
• 19. Meitzner, G., Mykyta, W.E.J. & Sinfelt, J.H. (1996). Methylamine hydrogenolysis on a rhodium catalyst-kinetics at high hydrogen partial pressures. Catal. Lett. 37, No.3-4,137-141. DOI: 10.1007/BF00807744. [Crossref]

Identifiers

DOI

10.2478/v10026-012-0082-5