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Research on Chemical Intermediates

, Volume 41, Issue 10, pp 6957–6966 | Cite as

A study about the synthesis of seven-membered-ring analogues of ketamine

  • Abolghasem MoghimiEmail author
  • Mohammad Reza Shahdadi
  • Sajjad Keshipour
  • Morteza Sadeghzadeh
Article

Abstract

Synthesis of seven-membered ring analogues of ketamine was studied with two strategies. In the first approach a sequence of five reactions was used which previously applied for ketamine synthesis. This strategy led to formation of 1-[(2-chlorophenyl)(methylimino)methyl]cyclohexan-1-ol as a precursor for the target molecule. In the second approach, we have designed and attempted to synthesize a new analogue of ketamine applying challenging reactions such as ring expansion and selective bromination. The result of this route is synthesis of some interesting compounds such as 6-phenyl-1-oxa-4-thiaspiro[4.6]undecane, 3-bromo-6-phenyl-1-oxa-4-thiaspiro[4.6]undecane and 2,7-dibromo-2-phenylcycloheptanone.

Keywords

Ketamine Phenylcycloheptanone Ring expansion Analgesia 

Notes

Acknowledgments

We gratefully acknowledge financial support from the Research Council of Imam Hossein University.

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Copyright information

© Springer Science+Business Media Dordrecht 2014

Authors and Affiliations

  • Abolghasem Moghimi
    • 1
    Email author
  • Mohammad Reza Shahdadi
    • 1
  • Sajjad Keshipour
    • 2
  • Morteza Sadeghzadeh
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceImam Hossein UniversityTehranIran
  2. 2.Department of Nanochemistry, Nanotechnology CenterUrmia UniversityUrmiaIran

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