GC-MS and IR Studies on the Six Possible Ring Regioisomeric Dimethylphenylpiperazines
The complete series of regioisomeric dimethylphenylpiperazines were synthesized and evaluated using GC-MS and FT-IR. The EI mass spectra show fragment ions characteristic of both the dimethylphenyl and the piperazine portions of the molecules. These fragments include the dimethylphenyl aziridinium cation at m/z 148 and dimethylphenyl cation at m/z 105. In addition, the low mass ion at m/z 56 for the C3H6N+ was observed in all piperazine EI spectra. Perfluoroacylation of the secondary amine nitrogen for each of the six regioisomers yielded amides whose mass spectra showed some differences in relative abundance of fragment ions without the appearance of any unique fragments. FTIR provides direct confirmation for differentiation of the six regioisomeric aromatic ring substituted dimethylphenylpiperazines. GC separation of this series of compounds was accomplished on an Rtx-200 column and retention appears related to the degree of steric crowding of the aromatic ring substituents.
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Document Type: Research Article
Publication date: March 1, 2017
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