Several compounds (in the free base form) with potential acetylcholine esterase inhibitory effects have been previously synthesized.  These compounds were converted into salts in order to make them water-soluble and in an attempt to resolve enantiomers present in a racemic mixture of one of the compounds.  Hydrochloride salts were prepared by dissolving the free base in sufficient volume of 0.5 M HCl in anhydrous isopropanol to contain 1.5-2 equivalents of HCl, chilling the solutions to maximize precipitation of the salt, and collecting the salt by pressure filtration under argon.  Several of these compounds have more than one amine group that could be protonated.  The number of equivalents of hydrochloric acid present in each compound was verified by potentiometric titration with sodium hydroxide.  Attempts are currently being made to prepare salts of the chiral compounds with different stereoisomers of tartaric acid and dibenzoyl tartaric acid.  Salts (and filtrates) were analyzed by <sup>1</sup>H-NMR and HPLC.

Salt formation of potential acetylcholine esterase inhibitors

249th National Meeting (2015)

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