100799-93-7Relevant academic research and scientific papers
Selective N-alkylation of primary amines with chloroacetamides under pH-controlled aqueous conditions
Loeser, Eric,Prasad, Kapa,Repic, Oljan
, p. 403 - 409 (2007/10/03)
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 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.
