Chemistry of Heterocyclic Compounds

, Volume 8, Issue 1, pp 70–74 | Cite as

Indole derivatives

LXXV. Mono-β-hydroxyethylation of tryptamines and synthesis of N,N′-bis[β-(3-indolyl)ethyl]ethylenediamines
  • I. D. Pletnev
  • N. P. Kostyuchenko
  • N. N. Suvorov
Article
  • 28 Downloads

Abstract

A method was developed for the mono-β-hydroxyethylation of tryptamines by the reaction of benzaltryptamine with ethylene iodohydrin in ethanol with subsequent hydrolysis of the intermediate quaternary ammonium salt to the corresponding dialkylamine. The alkylation of tryptamines with 1,2-dibromoethane gives N,N′-bis[2-(3-indolyl)ethyl]ethylenediamines.

Keywords

Ethylene Ammonium Hydrolysis Ethyl Organic Chemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. K. Mukerdzhi and N. N. Suvorov, Khim. Geterotsikl. Soedin., 74 (1972).Google Scholar
  2. 2.
    L. M. Orlova, M. N. Preobrazhenskaya, K. F. Turchin, Z. G. Starostina, and N. N. Suvorov, Zh. Organ. Khim., 5, 738 (1969).Google Scholar
  3. 3.
    G. Frangatos, G. Kohan, and F. L. Chubb, Can. J. Chem., 38, 1434 (1960).Google Scholar
  4. 4.
    J. K. Horner and W. A. Skinner, Can. J. Chem., 44, 315 (1966).Google Scholar
  5. 5.
    S.Wilkinson, J. Chem. Soc., 2079 (1958).Google Scholar
  6. 6.
    H. Decker and P. Becker, Ann., 395, 362 (1913).Google Scholar
  7. 7.
    T. Hoshino and J. Kotake, Ann., 516, 76 (1935).Google Scholar
  8. 8.
    J. N. Baxter and J. Cymerman-Craig, J. Chem. Soc., 1940 (1953).Google Scholar
  9. 9.
    K. Ward, J. Am. Chem. Soc., 57, 914 (1935).Google Scholar
  10. 10.
    Houben-Weyl, Meth. Org. Chem., G. Thieme, Stuttgart, 5/3, 862 (1962).Google Scholar
  11. 11.
    V. P. Potapov, A. P. Terent'ev, M. N. Preobrazhenskaya, and N. N. Suvorov, Zh. Obshch. Khim., 33, 2702 (1963).Google Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1974

Authors and Affiliations

  • I. D. Pletnev
    • 1
  • N. P. Kostyuchenko
    • 1
  • N. N. Suvorov
    • 1
  1. 1.F. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow

Personalised recommendations