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Synthesis of cycloalkyl analogues of antergan

University of British Columbia

Two series of cycloalkyl analogues of Antergan have been synthesized and analyzed. The compounds of the first series have the basic structure of N, N-dimethyl-N¹-phenyl-N¹ -(cycloalkylmethyl)-ethylenediamine in which the alkyl group was a propyl-, butyl-, pentyl-, hexyl-, or heptyl- ring structure. The second series of dicycloalkyl analogues has the general formula of N, N-dimethyl-N¹-cycloalkyl-N¹-(cycloalkylmethyl)-ethylenediamine in which both alkyl groups of propyl-, pentyl-, hexyl-, or heptyl- were the same ring size. Hydrochloride, picrate, and methyl iodide salts were prepared for these diamines, and for a number of the intermediates. In both series, the general reaction sequence followed was to start with the appropriate cycloalkyl carboxylic acid and build up to a secondary amine via an acid chloride and amide. The desired amine was then condensed with β-dimethylaminoethylbromide hydrobromide to form the tertiary diamine analogue. Two compounds, the dicyclohexyl- and dicycloheptyl-analogues, were formed by condensing the cycloalkylcarbonyl chloride with a substituted secondary ethylenediamine, and then reducing the amide with lithium aluminum hydride. Attempts to synthesize a sufficient quantity of the cyclo-octanecarboxanilide intermediate were unsuccessful. Difficulty was also encountered in preparing a stable and pure salt derivative for a number of the dicycloalkyl analogues. Signature of Examiners

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2011-10-14

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http://hdl.handle.net/2429/38000

Pharmaceutical Sciences

University of British Columbia

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