N,N-Dimethylaniline proceeded smoothly to afford the para-sulfonate 4j in a 70% isolated yield (84% conversion). The equivalent N,N-dimethylamine-propofol analogue to 5 is 12 did not show any evidence of reaction by crude 1 H NMR spectroscopy. A molecular model demonstrated how sterically compressed the sulfamate would be sandwiched between a di-ortho-isopropyl groups. Thus, sulfamation is necessary prior to sulfonation.