Article
Preparation of derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents
Irwin Becker,
Irwin Becker
Department of Chemistry, Villanova University, Villanova, PA 19085
Search for more papers by this authorIrwin Becker,
Irwin Becker
Department of Chemistry, Villanova University, Villanova, PA 19085
Search for more papers by this authorAbstract
This paper describes the preparation of twenty-eight derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents. In twenty-six of the preparations a chloro nitrogen heterocycle was caused to react with an excess of 1-(2-pyrimidinyl)piperazine in the absence of solvent. A specific example is given above.
References and Notes
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- 24 The structure of 29 was confirmed by a positive Beilstein test (C1 present), by CHN analyses, by an ir spectrum that indicated the presence of an aliphatic CN group in the molecule, and by a 1H nmr spectrum.
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- 27 The preparation of 24 had been reported earlier by Regnier, G.; Canevari, R.; LeDouarec, J.-C.; Laubie, M. Chimie Therapeutique 1972, 7, 192. But specific experimental details for the preparation of 24 are not given in this paper. Instead, details are given for the preparation of a compound of analogous structure. Apparently, then, they prepared 24 by refluxing a mixture of 1-(2-pyrimidinyl)piperazine and 6-chloropurine (2:1 mol ratio) in dimethylformamide (normal bp 153°) for 7 h. Their product, recrystallized from dimethylformamide, had mp greater than 350°. They give no spectral data for their product. Our preparation of 24 differed significantly from that of Regnier and coworkers. In our preparation a mixture of 6.05 g (0.0369 mol) of 1-(2-pyrimidinyl)piperazine and 1.90 g (0.0123 mol) of 6-chloropurine (3:1 mol ratio of amine to 6-chloropurine) was heated on the steam bath for 3.5 h, let stand for 67 h, heated on the steam bath for 4 h more, and let stand for 45 h. Our crude product gave a negative Beilstein test (no C1). It was recrystallized from the solvent pair of 95% ethanol and water. Our once recrystallized product gave an acceptable CHN analysis, and gave a 1H nmr spectrum that confirmed its structure.
- 28 Our product 26, prepared by cyanoethylation of 24, gave an acceptable CHN analysis, gave an ir spectrum that indicated the presence of an aliphatic CN group in the molecule, and gave a 1H nmr spectrum that confirmed its structure.
- 29 SciFinder lists no references for either 27 or 28 but does list five commercial sources for 27 and one commercial source for 28.
