Journal of Organic Chemistry p. 658 - 664 (1987)
Update date:2022-08-03
Topics:
Chi, Dae Yoon
Kilbourn, Michael R.
Katzenellenbogen, John A.
Welch, Michael J.
We have described a two-step method for the preparation of fluoroalkyl-substituted amines and amides.The sequence involves fluoride ion displacement of a haloalkyl trifluoromethanesulfonate (triflate), followed by fluoroalkylation of the heteroatom system (amine or amide) by the fluoroalkyl halide.Alternatively, the fluoroalkyl halide can be prepared by halofluorination of a terminal olefin.These reactions have been used to prepare various fluoroalkyl derivatives of N-phenylpiperazine and N-fluoroalkyl derivatives of the neuroleptic agent spiperone (7).The sequence is rapid, convenient, and efficient, even when fluoride ion is the limiting reagent.Therefore, it is readily adaptable to the preparation of a variety of compounds labeled with the short half-life (t1/2 = 110 min) positron-emitting radionuclide fluorine-18.
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