Date of Award

Spring 1981

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Roy L. Williams

Committee Member

Frank E. Scully, Jr.

Committee Member

Billy T. Upchurch

Committee Member

John D. Van Norman

Call Number for Print

Special Collections LD4331.C45 M354


Using the classical synthetic approach described by Maddox and co-workers43, the decyanation reaction of 1- piperidinocyclohexane carbonitrile (PCC), 5, was attempted using the heterocyclic anions of 2-methyl-5-nitropyridine, 22, 2-amino-5-nitropyridine, 23, and 2-hydroxy-5-nitropyridine, 24; however, the desired pyridine analogs of phencyclidine (PCP), 1, could not be prepared under these conditions. Attempts to prepare the same analogs via addition of these anions to the iminium tosylate and hydrobromide salts also proved unsuccessful.

The failure to observe the desired decyanation reaction has been attributed to the special sterochemical restrictions of the hindered nitrile of PCC in that facile displacement by the above heteroaromatic anions is impossible. The nucleophilic character of these anions together with their size can also be considered as contributing to their lack of reactivity.

A series of heterocyclic PCP analogs, 1-(1-phenyl-4- thiacyclohexyl) piperidine, 15, 1-(1-phenyl-N-methyl-4- piperidyl) piperidine, 16, and 1-(1-phenyl-4-oxacyclohexyl) piperidine, 20, was prepared from commercially available heterocyclic ketones via the classical synthetic approach described by Maddox.

A gross behavioral study of the potential activity of these analogs was carried out together with a specific measurement of their effects on motor performance as determined by the "Screen Test"53.

A general order of PCP-like activity was established using these techniques, and some structure-activity relationships could be assessed with regard to the potency and duration of action of certain of these analogs.


In Copyright. URI: This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).



Included in

Biochemistry Commons