Skip to main content
SpringerLink
Log in

Synthesis of N-methyl-N-(silylmethyl)amines

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

(Chloromethyl)silanes ClCH2SiMen(OMe)3-n (n = 0—2) react with methylamine at room temperature to give a mixture of secondary N-methyl-N-(silylmethyl)amines MeNHCH2SiMen(OMe)3-n and tertiary N-methy1-N, N-bis(silylmethyl)amines MeN[CH2SiMen(OMe)3-n]2 (n = 0—2). The product ratio depends on the ratio of the starting reactants. At the methylamine : silane ratio of 5 : 1, the main products are tertiary amines, while the increase in the proportion of methylamine (methylamine : silane = 25 : 1) leads to predomination of the secondary amines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J.-P. Picard, Can. J. Chem., 2000, 78, 1363.

    Article  CAS  Google Scholar 

  2. J.-P. Picard, Adv. Organomet. Chem., 2005, 52, 175.

    Article  CAS  Google Scholar 

  3. J. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev., 2008, 108, 2265.

    Article  CAS  PubMed  Google Scholar 

  4. N. W. Mitzel, K. Vojinovic, U. Losehand, in Organosilicon Chemistry V: From Molecules to Materials, Eds N. Auner, J. Weis, Wiley-VCH, Weinhiem, 2003, p. 226.

  5. J. O. Bauer, C. Strohmann, Inorg. Chim.Acta, 2018, 469, 133.

    Article  CAS  Google Scholar 

  6. S. G. Roller, J. O. Bauer, C. Strohmann, Angew. Chem., Int. Ed., 2017, 56, 7991.

    Article  CAS  Google Scholar 

  7. N. Resava-Reddy, C. Golz, C. Strohmann, R. Rumar, Chem. Eur. J., 2016, 22, 18373.

    Article  CAS  Google Scholar 

  8. V. H. Gessner, C. Strohmann, Dalton Trans., 2012, 41, 3452.

    Article  CAS  PubMed  Google Scholar 

  9. D. Fan, Y. Liu, J. Jia, Z. Zhang, Y. Liu, W. Zhang, Org. Lett., 2019, 21, 1042.

    Article  CAS  PubMed  Google Scholar 

  10. H. C. Jeong, S. H. Lim, D. W. Cho, S. H. Rim, P. S. Mariano, Org. Biomol. Chem., 2016, 14, 10502.

    Article  CAS  PubMed  Google Scholar 

  11. S. H. Lim, D. W. Cho, J. Choi, H. An, J. H. Shim, P. S. Mariano, Tetrahedron, 2017, 73, 6249.

    Article  CAS  Google Scholar 

  12. J.-J. Feng, M. Oestreich, Org. Lett., 2018, 20, 4273.

    Article  CAS  PubMed  Google Scholar 

  13. Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry, Ed. J. S. Clark, Oxford Univ. Press, 2002, p. 292.

    Google Scholar 

  14. J. Hernandez-Toribio, S. Padilla, J. Adrio, J. C. Carretero, Angew. Chem., Int. Ed., 2012, 51, 8854.

    Article  CAS  Google Scholar 

  15. P.-Q. Huang, Q.-W. Lang, X.-N. Hu, J. Org. Chem., 2016, 81, 10227.

    Article  CAS  PubMed  Google Scholar 

  16. G. Tran, R. Meier, L. Harris, D. L. Browne, S. V. Ley, J. Org. Chem., 2012, 77, 11071.

    Article  CAS  PubMed  Google Scholar 

  17. P. Srihari, S. R. Yaragorla, D. Basu, S. Chandrasekhar, Synthesis, 2006, 2646.

    Google Scholar 

  18. R.-I. Washizuka, S. Minakata, I. Ryu, M. Romatsu, Tetrahedron, 1999, 55, 12969.

    Article  CAS  Google Scholar 

  19. E. Ya. Lukevits, R. Ya. Sturkovich, Lzv. AN Latv. SSR [Bull. Acad. Sci. Latvian SSR], 1977, No. 7, 29 (in Russian).

    Google Scholar 

  20. V. P. Feshin, L. S. Romanenko, M. G. Voronkov, Russ. Chem. Rev., 1981, 50, 248.

    Article  Google Scholar 

  21. G. Zingler, H. Relling, E. Popowski, Z. Anorg. Allg. Chem., 1981, 476, 41.

    Article  CAS  Google Scholar 

  22. V. Fialova, V. Bažant, V. Chvalovsky, Coll. Czech. Chem. Commun., 1973, 38, 3837.

    Article  CAS  Google Scholar 

  23. N. W. Mitzel, C. Riener, D. W. H. Rankin, Organometallics, 1999, 18, 3437.

    Article  CAS  Google Scholar 

  24. N. W. Mitzel, R. Vojinovic, T. Foerster, H. E. Robertson, R. B. Borisenko, D. W. H. Rankin, Chem. Eur. J., 2005, 11, 5114.

    Article  CAS  PubMed  Google Scholar 

  25. B. Waerder, S. Steinhauer, C. G. Reuter, J. Bader, B. Neumann, H. G. Stammler, Yu. V. Vishnevskiy, B. Hoge, N. W. Mitzel, Dalton Trans., 2015, 44, 13347.

    Article  CAS  PubMed  Google Scholar 

  26. A. Berkefeld, C. F. Guerra, R. Bertermann, D. Troegel, J. O. Daiss, J. Stohrer, F. M. Bickelhaupt, R. Tacke, Organometallics, 2014, 33, 2721.

    Article  CAS  Google Scholar 

  27. J. Ehbets, S. Lorenzen, C. Mahler, R. Bertermann, A. Berkefeld, J. Poater, E. Fritz-Langhals, R. Weidner, F. M. Bickelhaupt, R. Tacke, Eur. J. Inorg. Chem., 2016, 1641.

    Google Scholar 

  28. N. W. Mitzel, C. Riener, D. W. H. Rankin, Organometallics, 1999, 18, 3437.

    Article  CAS  Google Scholar 

  29. N. F. Lazareva, Russ. Chem. Bull, 2011, 60, 615.

    Article  CAS  Google Scholar 

  30. R. Tacke, R. Bertermann, A. Biller, O. Dannappel, M. Pülm, R. Willeke, Eur. J. Inorg. Chem., 1999, 795.

    Google Scholar 

  31. L.-L. Bao, Z.-Q. Liu, Chem. Med. Chem., 2016, 11, 1617.

    Article  CAS  PubMed  Google Scholar 

  32. J. Chen, T. Chen, Q. Hu, R. Püntener, Y. Ren, J. She, Z. Du, M. Scalone, Org. Process Res. Dev., 2014, 18, 1702.

    Article  CAS  Google Scholar 

  33. I. V. Sterkhova, I. M. Lazarev, V. I. Smirnov, N. F. Lazareva, J. Organomet. Chem., 2015, 775, 27.

    Article  CAS  Google Scholar 

  34. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, 6th ed., Butterworth-Heinemann, Amsterdam–Boston, 2009, 760 pp.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    B. A. Gostevskii & N. F. Lazareva

Authors
  1. B. A. Gostevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. F. Lazareva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. F. Lazareva.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gostevskii, B.A., Lazareva, N.F. Synthesis of N-methyl-N-(silylmethyl)amines. Russ Chem Bull 68, 1555–1557 (2019). https://doi.org/10.1007/s11172-019-2591-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2591-3

Key words

Search

Navigation