SELECTIVE N-ALKYLATION OF PRIMARY AMINES WITH CHLOROACETAMIDES UNDER pH-CONTROLLED AQUEOUS CONDITIONS
作者:Eric Loeser、Kapa Prasad、Oljan Repic
DOI:10.1081/scc-120002124
日期:——
A practical method for selective alkylation of primary amines with chloroacetamides under modified Finkelstein conditions using stoichiometric amounts of sodium iodide in acetonitrile/water is described. An interesting finding in this study was that alpha-alkylaminoacetamides are less basic than the corresponding primary alkylamines by about 2pKa units; this necessitated a pH of 12 during alkylation to optimize the monoalkylation selectivity. Depending on the amount of primary amine used, mono: dialkylation selectivities ranged from 2.7 to 10.