Synthesis and Characterization of a Series of 1-Aryl-4-[Aryldiazenyl]-piperazines. Part II1. 1-Aryl-4-(2-Aryl-1-Diazenyl)-piperazines with Fluoro-, chloro-, Methyl-, Cyano- and Acetyl Substituents in The 1-Aryl Group



Karen O’Malleya, *, Keith Vaughanb, *
a ALS Environmental, Calgary, AB Canada
b Department of Chemistry, Saint Mary’s University Halifax, Nova Scotia B3H 3C3, Canada


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© O’Malley and Vaughan; Licensee Bentham Open.

open-access license: This is an open access article licensed under the terms of the Creative Commons Attribution-Non-Commercial 4.0 International Public License (CC BY-NC 4.0) (https://creativecommons.org/licenses/by-nc/4.0/legalcode), which permits unrestricted, non-commercial use, distribution and reproduction in any medium, provided the work is properly cited.

* Address correspondence to these authors at the Department of Chemistry, Saint Mary’s University Halifax, Nova Scotia B3H 3C3; Phone: (902)-420-5650; Fax: (902)-496-8104; E-mail: keith.vaughan@smu.ca, karen.omalley@alsglobal.com
1 For part I in this series please see the Open Org Chem J, 2015, 9, 35-42.


Abstract

This paper reports the synthesis and characterization of eight series of 1-aryl-4-(2-aryl-1-diazenyl)-piperazines (12 to 19). Several series of these triazenes have been synthesized by the diazotization of a primary arylamine followed by diazonium coupling with a secondary arylpiperazine . The arylpiperazines used in this study are: 1-phenylpiperazine, 1-(4-fluorophenyl-)piperazine, 1-(4-chlorophenyl-)piperazine, 1-(3,4-dichlorophenyl-)piperazine, 1-(2-methylphenyl-)-piperazine, 1-(4-acetophenyl-)-piperazine, 1-(2-pyridyl-)piperazine and 2-cyanophenylpiperazine. These new triazenes (series 12-19) have been identified with a cocktail of contemporary spectroscopic techniques, notably infra-red and nuclear magnetic spectroscopy, supported by high resolution electron ionization mass spectrometry.

Keywords: 1-Arylpiperazine, Aryldiazenylpiperazines, Diazonium Coupling, IR spectroscopy, Mass Spectrometry, NMR, Triazene.