Development of (/sup 18/F)halofluorination and (/sup 18/F)fluoride ion displacement reactions for the synthesis of F-18 labelled radiopharmaceuticals

Thesis/Dissertation · Wed Jan 01 04:00:00 EST 1986

OSTI ID:6558213

Chi, D Y

Two fluorine-18 labeling methods, (/sup 18/F)halofluorination and (/sup 18/F)fluoride ion displacement reactions, have been developed to assess their potential for labeling molecules with the positron-emitting radionuclide fluorine-18 at the no-carrier-added level. Olefin halofluorination involves the in situ generation of a halogen-fluoride reagent and subsequent addition to an olefin. The characteristics of this reaction were investigated with three model olefins (allylbenzene, 1-hexene, and propene). A two-step method for the preparation of fluoroalkyl substituted amines and amides has been achieved. The sequence involves fluoride ion displacement of trifluoromethanesulfonates (triflates) from short-chain haloalkyl triflates, followed by fluoroalkylation of the amine or amide. Alternatively, short-chain fluoroalkyl halides can be prepared by halofluorination of a terminal olefin. These reactions have been used to prepare various fluoroalkyl derivatives of 1-phenylpiperazine and N-fluoroalkyl derivatives of the neuroleptic agent spiperone. A series of fluorine-18 labeled N-fluoroalkylated spiperone derivatives were synthesized by N-alkylation of spiperone with fluoroalkyl halides.

• Research Organization: Illinois Univ., Urbana (USA)
• OSTI ID: 6558213
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
ALKENES
AMIDES
AMINES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
DRUGS
FLUORINE 18
FLUORINE ISOTOPES
HOURS LIVING RADIOISOTOPES
HYDROCARBONS
ISOTOPES
LABELLED COMPOUNDS
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
RADIOISOTOPES
RADIOPHARMACEUTICALS
SYNTHESIS