SYNTHESIS OF NEW DERIVATIVES OF PHENYLOXYPROPARGYL PIPERIDINES

Abstract

4-(3-phenoxyprop-1-yn-1-yl)piperidine-4-ol has been obtained by condensation of 1-methyl-piperidine-4-one with phenoxypropargyl in the Favorsky reaction conditions in absolute benzene, in the presence of a fivefold excess of powdered technical KOH at the ratio of piperidone-4:phenoxypropargyl = 1:1.5. Upon acylation of tertiary phenoxypropynyl piperidol by cyclobutane-, cyclopentane-, cyclohexanecarbonyl chlorides in dioxane at the room temperature or upon heating, the corresponding hydrochlorides of esters have been formed. The structure of the synthesized compounds has been confirmed by the NMR and X-ray spectroscopy data.

References

[1] Bryan L. Antimicrobial drug resistance. Orlando: Academic press, 1984. P. 450.
[2] Regev-Yochay G, Raz M, Dagan R, Roizin H, et al. Reduction in antibiotic use following a cluster randomized controlled multifaceted intervention: the Israeli judicious antibiotic prescription study // Clinical Infectious Diseases. 2011. Vol. 53(1). P. 33-41.
[3] Antimicrobial resistance surveillance in Europe 2012. Annual Report of the European Antimicrobial Resistance Surveillance Network (EARS-Net). European Centre for Disease Prevention and Control. Introduced 2013. Stockholm. P. 208.
[4] Shostakovskiy M.F., Vlassov V.М., Kuznetsova Т.S., Safronovaа L.А. New field of application of the A.Ye. Favorskiy reaction // J. of Org. Chem. 1966. N 2. P. 953-956.
[5] Azerbayev I.N., Yerzhanov K.B., Sadykov Т.S., Mussin М.А., Umarova Z.N. Interaction of butoxypropargyls with carbonyl compounds // Izv. AS KazSSR, Chemical Series. 1976. N 1. P. 30-33.
[6] Yokubaitite S.P., Koudis Z.P., Mozolis V.V. Synthesis and properties of acetylene derivatives on the basis of phenyloxypropargyl // Works of AS Lith. SSR, Series B. 1980. N 1. P. 116-119.
[7] Kurbanov F.K., Kuchkarov А.V., Agzamov K.А., Dzhurakulov G. Synthesis of acetylene alcohols on the basis of propargyl ester of phenols // Report of AS Uzb.SSR. 1972. N 1. P. 38-39.
[8] Bazhykova K.B., Praliyev K.D., Poplavskaya I.А. Synthesis and some transformations of 1-(2-ethoxyethyl)-4-(3-aryloxypropyn-1-yl)piperidines // Ivz. of RK MS-AS. Series Chem. 1998. N 3. P. 112-120.
[9] Kozlovskiy V.I., Praliyev K.D., Goncharuk V.V., Zavodnik L.B., Akhmetova G.S., Iskakova Т.K., Yu V.K. An analgesic activity of original substances of the piperidine series: experimental study on the model of thermal secomposition // Journal of the Grodno Medical University. Belarus, 2014. N 3. P. 38-41.
[10] Akhmetova G.S., Sadyrbayeva F.M., Yu V.K., Praliyev K.D., Zhilkibayev O.T., Pichkhadze G.M., Nassyrova S.R., Imashova Sh.O., Amirkulova M.K. Piperidine-containing derivatives of cyclopropanecarboxylic acid – potential PAS // Chem. J. of Kazakhstan. 2012. N 1. P. 118-127.
[11] Sadyrbayeva F.M., Ospanova S.I., Issayeva U.B., Akhmetova G.S., Yu V.K., Praliyev K.D. Amides of cyclopropanecarboxylic acid – potential BAS // Cluster of Conferences in organic chemistry “OrtChim”-2013. June 17-21, 2013. SPt.: Repino. P. 248-249.
[12] Kumar K. Ajar. Brief review on cyclopropane analogs: synthesis and their pharmacological applications // Int. J. of Pharm. and Pharmac. Sc. 2012. N 5(1). P. 467-472.
[13] RK Innovation patent No.31047. Hydrochloride of 1-methyl-4-(3-phenoxypropin-1-yl)-4cyclopropanecarbonyloxypiperidine, possessing an antibacterial activity // K.D. Praliyev, M.Ye. Kulmanov, A.I. Ilyin, F.M. Sadyrbayeva, G.S. Akhmetova, V.K. Yu, U.B. Issayeva, N.V. Leonova, O.A. Sulzhik, S.S. Kassymbekova. Published 15.04.16. Bul. N 4.
[14] Akhmetova G.S, Sadyrbayeva F.М., Issayeva U.B., Praliyev K.D., Seilkhanov Т.М., Yu V.K., Sultanov D.А. Directed synthesis of С- and N-substituted phenyloxypropynylpiperidines of an antiinfective activity // Herald of KarSU. Chemical Series, 2017. N 3(87). P. 56-63.