Abstract
Reaction of N-ethylpiperid-4-one with benzaldehyde and KOH in 65% aqueous methanol gives 2,7-diethyl-10a-hydroxy-9-phenyl-4-(phenylmethylene)-2,7-diaza-10-oxa-1,2,3,4,5,6,7,8,8a, 10a-decahydroanthracene. In the presence of HCl/EtOH, 3,5-bis(phenylmethylene)-1-ethylpiperid-4-one is formed. In the presence of HCl/AcOH, 2,7-diethyl-9-phenyl-4,5-bis(phenylmethylene)-2,7-diaza-10-oxa-1,2,3,4,5,6,7,8-octahydroanthracene is formed.
Similar content being viewed by others
References
L. N. Koikov, N. V. Alexeeva, N. B. Grigor'ev, V. I. Levina, K. F. Turchin, T. Ya. Filipenko, I. S. Severina, I. K. Ryaposova, and V. G. Granik, Mendeleev Commun., No. 3, 94 (1996).
L. N. Koikov, N. V. Alekseeva, V. I. Levina, N. B. Grigor'ev, K. F. Turchin, T. Ya. Filipenko, M. D. Mashkovskii, M. E. Kaminka, V. B. Nikitin, G. E. Engalycheva, M. A. Kalinkina, I. S. Severina, I. K. Ryaposova, and V. G. Granik, Khim.-Farm. Zh., No. 5, 28 (1997).
G. M. Kuettel and S. M. McElvain, J. Am. Chem. Soc.,53, 2692 (1931).
Swiss. Pat. 594,667 J. Kapacho and C. F. Turk, Chem. Abstr.,88, 136,616 (1978).
S. C. Dickerman and H. G. Limdwall, J. Org. Chem.,14, 530 (1949).
Pat. 2,430,590 Germany. J. Kapacho and C. F. Turk, Chem. Abstr.,82, 170,915 (1975).
S. M. McElvain and K. Rorig, J. Am. Chem. Soc.,70, 1820 (1948).
J. L. Nelson and N. L. David, J. Am. Chem. Soc.,77, 1852 (1955).
G. G. Lyle, J. J. Dziark, J. Connor, and C. S. Huber, Tetrahedron,29, 4039 (1973).
Additional information
Center for the Chemistry of Medicinal Agents, All-Russian Chemicopharmaceutical Institute, Moscow 119815. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1247–1249, September, 1998.
Rights and permissions
About this article
Cite this article
Alekseeva, N.V., Koikov, L.N. & Turchin, K.F. Condensation of N-ethylpiperid-4-one with benzaldehyde. Chem Heterocycl Compd 34, 1070–1072 (1998). https://doi.org/10.1007/BF02251553
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02251553