Issue

Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

Copyright (c) 2015 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Novel Route for Synthesis of (S)-1-Benzyl-6-oxopiperidine-2-carboxylic Acid and its Crystal Structure

https://doi.org/10.14233/ajchem.2015.18648
J. Sivý
Institute of Mathematics and Physics, Faculty of Mechanical Engineering, Slovak University of Technology, Námestie slobody 17, SK-81231 Bratislava, Slovak Republic
V. Vrábel
Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic
Š. Marchalín
Institute of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic
P. Šafár
Institute of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic

Corresponding Author(s) : J. Sivý

julius.sivy@stuba.sk

Asian Journal of Chemistry, Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015

Abstract

A piperidine carboxylic acid was synthesized and the structure of compound was confirmed by spectral methods and the X-ray diffraction experiment was employed to investigate the crystal structure of (S)-1-benzyl-6-oxopiperidine-2-carboxylic acid. In the crystal structure of the title compound 5, C13H15NO3, one molecule creates independent part of the unit cell. The compound crystallizes in the orthorhombic space group P212121 with a = 8.1384(3), b = 10.5953(3), c = 14.1104(3) Å and a = b = g = 90º. The piperidine ring exhibits a chair conformation. The mean plane of the piperidine ring makes a dihedral angle of 61.10(9)º with the planar benzyl ring. The crystal structure packing of the compound is controlled by strong intermolecular O-H···O hydrogen bonds and weak C-H···O intramolecular interactions.

Keywords

Synthesis Oxopiperidine-carboxylic acid Single-crystal X-ray study R factor = 0.0296
Sivý, J., Vrábel, V., Marchalín, . Š., & Šafár, P. (2015). Novel Route for Synthesis of (S)-1-Benzyl-6-oxopiperidine-2-carboxylic Acid and its Crystal Structure. Asian Journal of Chemistry, 27(7), 2635–2638. https://doi.org/10.14233/ajchem.2015.18648
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. O.P.W. Robinson, Postgrad. Med. J., 49(Suppl.), 9 (1973).
  2. C. Hootelé, B. Colau, F. Helin, J.P. Declerq, G. Germain and M. Van Meerssche, Tetrahedron Lett., 21, 5063 (1980); doi:10.1016/S0040-4039(00)71135-X.
  3. Z. Jia, J.W. Quail, V.K. Arora and J.R. Dimmock, Acta Crystallogr. C, 45, 285 (1989); doi:10.1107/S0108270188011345.
  4. Z. Jia, J.W. Quail, V.K. Arora and J.R. Dimmock, Acta Crystallogr. C, 45, 1117 (1989); doi:10.1107/S0108270189000569.
  5. C.J. Cheer, J.P. Cosgrove and B.M. Vittimberga, Acta Crystallogr. C, 40, 1474 (1984); doi:10.1107/S0108270184008404.
  6. K. Sekar, S. Parthasarathy and T.R. Radhakrishnan, Acta Crystallogr. C, 46, 1338 (1990); doi:10.1107/S0108270190002220.
  7. K. Sekar, S. Parthasarathy and T.R. Radhakrishnan, Acta Crystallogr. C, 49, 93 (1993); doi:10.1107/S0108270192004207.
  8. J.N. Moorthy and K. Venkatesan, Bull. Chem. Soc. Jpn., 67, 1 (1994); doi:10.1246/bcsj.67.1.
  9. E. Diaz, H. Barrios and R.A. Toscano, Acta Crystallogr. C, 53, 1468 (1997); doi:10.1107/S0108270197002953.
  10. J. Perumattam, B.G. Shearer, W.L. Confer and R.M. Mathew, Tetrahedron Lett., 32, 7183 (1991); doi:10.1016/0040-4039(91)80471-H.
  11. T.K. Jones, S.G. Mills, R.A. Reamer, D. Askin, R. Desmond, R.P. Volante and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989); doi:10.1021/ja00185a071.
  12. S.N. Sehgal, H. Baker, C.P. Eng, K. Singh and C. Véezina, J. Antibiot., 36, 351 (1983); doi:10.7164/antibiotics.36.351.
  13. J. Martens and M. Scheunemann, Tetrahedron Lett., 32, 1417 (1991); doi:10.1016/0040-4039(91)80345-7.
  14. J.R. Dimmock, V.K. Arora, S.L. Wonko, N.W. Hamon, J.W. Quail, Z. Jia, R.C. Warrington, W.D. Fang and J.S. Lee, Drug Des. Deliv., 6, 183 (1990).
  15. B. Mutus, J.D. Wagner, C.J. Talpas, J.R. Dimmock, O.A. Phillips and R.S. Reid, Anal. Biochem., 177, 237 (1989); doi:10.1016/0003-2697(89)90045-6.
  16. C. Narajji, M.D. Karvekar and A.K. Das, Asian J. Chem., 20, 6183 (2008).
  17. B. Gunasekaran, S. Kathiravan, R. Raghunathan and V. Manivannan, Asian J. Chem., 25, S51 (2013); doi:10.14233/ajchem.2013.14935.
  18. V. Vrábel, J. Sivý, P. Šafář and Š. Marchalín, Acta Crystallogr. C, 70, 817 (2014); doi:10.1107/S2053229614016301.
  19. G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
  20. M.C. Burla, R. Caliandro, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, M. Mallamo, A. Mazzone and G. Polidori, SIR2014 (2014) (Submitted).
  21. K. Brandenburg, DIAMOND, Crystal Impact GbR, Bonn, Germany (2001).
  22. Ch.B. Hübschle, G.M. Sheldrick and B. Dittrich, J. Appl. Cryst., 44, 1281 (2011); doi:10.1107/S0021889811043202.
  23. L.J. Farrugia, J. Appl. Cryst., 45, 849 (2012); doi:10.1107/S0021889812029111.
  24. A.L. Spek, Acta Crystallogr. D Biol. Crystallogr., 65, 148 (2009); doi:10.1107/S090744490804362X.
  25. M. Nardelli, J. Appl. Cryst., 28, 659 (1995); doi:10.1107/S0021889895007138.
  26. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard and H. Puschmann, J. Appl. Cryst., 42, 339 (2009); doi:10.1107/S0021889808042726.
  27. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975); doi:10.1021/ja00839a011.
  28. J. Bernstein, R.E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem. Int. Ed. Engl., 34, 1555 (1995); doi:10.1002/anie.199515551.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0