Секция 7 Химия и химическая технология (на иностранном языке)
209
Getting benzhydrylamine by reduction
reaction of benzophenone oxime
N.V. Danilenko, V.Y. Kuksenok
Scientific supervisor – V.V. Shtrykova, Assoc. Prof, PhD in Chemistry;
Linguistic advisor – L.V. Maletina, Assoc. Prof, PhD in Pedagogical Science
Tomsk Polytechnic University
634050, Russia, Tomsk, 30 Lenin Avenue, [email protected]
Benzhydrylureas are known as biologically active substances with a
pronounced anticonvulsive action, which are used as pharmaceuticals [1].
The initial substrates in their synthesis can be benzhydrylamines, whose production is quite problematic. Among the previously developed methods of
benzhydrylamines production, the reductive amanation according to the reaction of Leuckart-Valloha:special is deserved special attention.
Unfortunately, this method has several disadvantages, such as high temperature and the process duration. Thus it is necessary to develop an easy-touse method for the obtaining of targeted amine (2).
Methods
We paid attention to the possibility of the synthesis of the amine (2)
through a reductive amination reaction using hydroxylamine as the process
is conducted at temperatures up to 100 °C and its duration is smaller than in
the case of the Leuckart-Wallach reaction. Therefore, the first stage of the
research work was to obtain benzophenone oxime (4) [2], the second is its recovery to the amine (2). As a redox system we used sodium metal in IPA [3].
Results and discussion
Oxime , as the substrate for the corresponding amine production, was
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XV Международная научно-практическая конференция имени профессора Л.П. Кулёва
obtained by the reaction of benzophenone with hydroxylamine (4).
Тm.p. = 142(142), 1Н NMR (СDCl3, 300 MHz, ppm), δm.g.: 7.34–7.39 (m,
5H), 7.47–7.49(m, 5H)
To restore oxime (4) to the amine (2) various systems such as
NaBH4 [4]; NaBH4/AcOH; NaBH4/H2SO4; Na2S/NaHCO3; Na2S/MeOH;
Fe2O3/C6H6; Fe@C/ NaCO3; Zn/AcOH; Na/IPA have been tested.
However, benzhydrylamine formation was recorded only in the case of
Na/IPA.
In the future we are planning to replace the IRA by high boiling alcohol,
it is possible to increase the yield of the targeted product (2).
References
1. Petchenkin A.G., Tignibidina L.G., Gorshkov V.K. // Pharmaceutical Chemistry
Journal, 1979.– №5.– P.57–59.
2. Agranomov A.E., Shabarov Y.S., Laboratory work in organic workshop.– M.:
Chemistry, 1974.– P.375.
3. E.B. Tsupak. Methods of preparation of amines.– Rostov-on-Don, 2001.– P.7.
4. Thor Håkon Krane Thvedt , Erik Fuglseth, Eirik Sundby, Bård Helge Hoff,
Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution
and limitations to the Mitsunobu inversion protocol. // Tetrahedron, 2010.–
№66.– P.6733–6743.
Dunites from the Kytlym massif as perspective raw
materials for ceramic proppants production
L.P. Govorova, A.Y. Tokareva
Supervisor – doctor of technical sciences, professor, T.V. Vakalova;
Linguist – candidate of pedagogic sciences, docent, L.V. Maletina
Tomsk polytechnic university
634050, Russia, Tomsk, 30 Lenin Avenue, [email protected]
Magnesium silicate is one of the most important kinds of ceramic raw
materials. Its occurrences are widespread and stock numbers billions of
tons. Among the wide variety of magnesium silicates (forsterite, fayalite,