The formation of the alkylammonium salts 5 and 6 is likely due to low reactivity of 3i, j with 2a, b in refluxing tetrahydrofuran, and the resulting long times of the attempted reaction may have resulted in the admission of adventitious moisture (Table I). Under conditions of shorter reaction times, considerable starting material remained. In a control experiment pure 4j was subjected to the workup conditions of the N-trifluoroacetylation reactions, but no hydrolysis ...
[Steffel, Lauren R.; Cashman, Timothy J.; Reutershan, Michael H.; Linton, Brian R. Journal of the American Chemical Society, 2007 , vol. 129, # 43 p. 12956 - 12957]