A method, whereby primary and secondary amines are exhaustively alkylated to their quaternary stage in a one-step procedure, has been extended to a broad spectrum of amines. The study synthetically utilizes the fact that protonation of sterically hindered amines is affected only slightly by steric hindrance, whereas nucleophilicity as measured by the rate of alkylation is considerably decreased. A sterically hindered organic base of greater base strength than the reactant amines is employed to bind the acid that is generated in alkylation reactions. Selection of an appropriate organic base as the proton acceptor enables complete alkylation of primary and secondary aromatic amines with pKa values as low as 2.36 and alicyclic and strong aliphatic amines with pKa values as high as 11.1. The mild and homogeneous reaction conditions result in good yields with minimal laboratory manipulations and effort. The method is of particular importance for reactions in which the amines and the alkylating agents possess labile functions.

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