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UBC Theses and Dissertations

Synthesis of cycloalkyl analogues of antergan Wang, Yih Song


Cycloalkyl analogues of Antergan with the basic structure of N, N-dimethyl-N’-cycloalkylmethyl-N’-phenylethylenedi-amlne have been synthesized in good yields. The alkyl group was a butyl-, pentyl-, hexyl-, or heptyl-ring structure. The compounds with the benzyl group of Antergan substituted by a hydrogen or a methyl group were also synthesized in good yields. The general reaction sequence followed was to start with the appropriate cycloalkanecarboxyllc acid and build up to a secondary amine via an acid chloride and an amide. Leung’s methods (1) were followed and checked up to this step. Further reaction sequences were developed during this study. The desired amine was reacted with chloroacetyl chloride, dimethylamine and then reduced to the tertiary diamine analogues. The preliminary antihistamine activity of these analogues was studied and compared with that of Diphenhydramine Hydrochloride Standard Solution. The relative activity of each analogue was also determined.

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