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Synthesis of adamantyl-containing phenylpiperidines

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Chemistry of Heterocyclic Compounds Aims and scope

The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)-phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method.

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This work was supported by a grant from the Russian Scientific Fund (project No. 15-13-0084).

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeiskaya St., Samara, 443100, Russia

    Vera A. Shadrikova, Evgeny V. Golovin, Vadim A. Shiryaev, Marat R. Baimuratov & Yuri N. Klimochkin

  2. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Victor B. Rybakov

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  1. Vera A. Shadrikova
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  2. Evgeny V. Golovin
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Correspondence to Vera A. Shadrikova.

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The Supplementary information file containing the data of 1H and 13C NMR spectra, 1H–13C HMBC, 1H–13C HETCOR, and NOESY two-dimensional NMR experiments for compounds 2a–f, 4a–е, as well as the log files for calculating the energy of conformers 4b–е is available online at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 891–898

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Shadrikova, V.A., Golovin, E.V., Shiryaev, V.A. et al. Synthesis of adamantyl-containing phenylpiperidines. Chem Heterocycl Comp 51, 891–898 (2015). https://doi.org/10.1007/s10593-015-1792-4

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