![Sample our Physical Sciences journals, sign in here to start your FREE access for 14 days]({"type":"image" , "src" : "/sda/110819/TOC-Subject-Sample-2021-Physical-Sciences.jpg"})
ABSTRACT
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 α-alkylaminoacetamides are less basic than the corresponding primary alkylamines by about 2 pKa 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.