N-alkylation of N-heterocyclic ionic liquid precursors in ionic liquids

Abstract

The room temperature ionic liquids [BMIM][PF6] and [P14][Tf2N] in conjunction with KOH are superior reaction media for the alkylation of the secondary amine 3-azabicyclo[3.2.2]nonane under mild conditions. The factors examined were alkyl halide chain length (C1 to C4) and halide identity (Cl, Br, I). The tertiary amine products are released from the reaction medium as a separate layer and can be isolated in good yields by simple decantation.