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This paper describes the molecular shuttling and specific N-acylations of a [2]rotaxane featuring an encircling crown ether unit and both N-alkylaniline and N,N-dialkylamine centers on its dumbbell-shaped component. The crown binds predominantly to the dialkylammonium center under neutral conditions. Reactions with acid anhydride in nonpolar solvents and in the absence or presence of a weak base resulted in the N-acylations occurring mainly at the aniline moiety, and selective N-acylations of the dialkylamine unit occurred in polar solvents in the presence of strong bases.