Abstract
4-Cyano-4-dimethylamino-1,3-dimethylpiperidines and 4-cyano-4-dimethylamino-1,2,5-trimethylpiperidines have been synthesized and the directions of their reactions with nucleophilic reagents (Grignard reagents, organolithium compounds, lithium tetrahydroaluminate, etc.) have been studied. Depending on the nature of the reagent, the reactions of the α-amino nitriles take place by addition to the cyano group, by its replacement, or by these two directions simultaneously.
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Literature cited
C. van de Westeringh, P. van Daele, B. Hermans, C. van der Eycken, J. Boey, and P. A. J. Janssen, J. Med. Chem., 7, 619 (1964).
B. Hermans, P. van Daele, C. van de Westeringh, C. van der Eycken, J. Boey, and P. A. J. Janssen, J. Med. Chem., 8, 851 (1965).
B. Hermans, P. van Daele, C. van de Westeringh, C. van der Eycken, J. Boey, and P. A. J. Janssen, J. Med. Chem., 9, 49 (1966).
V. A. Zagorevskii and K. I. Lopatina, Zh. Obshch. Khim., 1, 1500 (1965).
E. S. Nilit-skaya, L. M. Alekseeva, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., 1672 (1971).
I. N. Nazarov and B. V. Unkovskii, Zh. Obshch. Khim., 26, 3181 (1956).
B. V. Unkovskii, G. S. Gusakova, and I. A. Mokhir, Zh. Obshch. Khim., 30, 3926 (1960).
J. Houben, Methoden der Organischen Chemie, Vol. 4 [Russian translation], Goskhimizdat, Moscow (1949), p. 851.
Z. Welvart, Compt. Rend., 238, 2536 (1954).
G. Chauviere, B. Thoubar, and Z. Welvart, Bull. Soc. Chim. Fr., 1428 (1963).
G. Chauviere, W. Vetter, and Z. Welvart, Compt. Rend., 258, 4287 (1964).
I. Canceill and J. Jacques, Bull. Soc. Chim. Fr., 903 (1965).
Z. Welvart, Compt. Rend., 250, 1870 (1960).
J. Sansoulet, C. Takx, and Z. Welvart, Compt. Rend., 250, 4370 (1960).
H. R. Henze, G. L. Sutherland, and G. B. Roberts, J. Amer. Chem. Soc., 79, 6230 (1957).
H. M. Taylor and C. R. Houser, J. Amer. Chem. Soc., 82, 1960 (1960).
G. F. Morris and C. R. Houser, J. Org. Chem., 27, 465 (1962).
L. Bellamy, Infrared Spectra of Complex Molecules, 2nd ed., Methuen (1958).
M. Thies, H. Schönenberger, and P. K. Qasba, Tetrahedron Lett., 163 (1965).
W. McMeeking and T. S. Stevens, J. Chem. Soc., 347 (1933).
G. Le Ny and Z. Welvart, Compt. Rend., 245, 434 (1957).
M. Mousseron, J. M. Bessiere, P. Geneste, J.-M. Kamenka, and J. Marti, Bull. Soc. Chim. Fr., 3863 (1968).
M. Mousseron, J.-M. Kamenka, and M. R. Darvich, Bull. Soc. Chim. Fr., 208 (1970).
I. N. Nazarov, A. V. Kamernitskii, and A. A. Akhrem, Zh. Obshch. Khim., 28, 1458 (1958).
E. W. Garbish and D. B. Patterson, J. Amer. Chem. Soc., 85, 3228 (1963).
J. Alleon and Z, Welvart, Bull. Soc. Chim. Fr., 1247 (1965).
J. Alleon-Aimi, D. Cabaret, I.-P. Mazaleyrat, and Z. Welvart, Bull. Soc. Chim. Fr., 4235 (1968).
R. Granger and H. Techer, Bull. Soc. Chim. Fr., 787 (1960).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1224–1231, September, 1973.
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Unkovskii, B.V., Matyukhin, Y.S., Malina, Y.F. et al. Synthesis of 4-Cyano-4-dimethylamino-1,3-dimethyl-piperidines and 4-cyano-4-dimethyl-1,2,5-trimethyl-piperidines and investigation of features of their reactions with some nucleophilic reagents. Chem Heterocycl Compd 9, 1112–1118 (1973). https://doi.org/10.1007/BF00474784
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DOI: https://doi.org/10.1007/BF00474784