Amino-functionalized ionic liquid as a nucleophilic scavenger in solution phase combinatorial synthesis

A new functionalized ionic liquid, 1-aminoethyl-3-methylimidazolium hexafluorophosphate was synthesized from 1-methylimidazole and 2-bromoethylamine hydrobromide. This ionic liquid was found to be an efficient scavenger for removing excess electrophiles, such as benzoyl chloride, p-toluenesulfochloride, phenyl isothiocyanate, and p-chlorophenyl isocyanate, in a solution-phase parallel synthesis. The resulting ionic liquid derivatives can be separated directly from the reaction mixture. Desired products were obtained with high purity. Only 1.5-2.0 equiv of this scavenger was needed with a sequestration time of less than 35 min. In addition, the used ionic liquid can be regenerated and recycled several times without significant loss of activity.