A comparison of the incorporation of 123I and 18F into 1‐[1‐(3‐hydroxyphenyl) cyclohexyl]‐4‐(methanesulfonyloxy)piperidine by nucleophilic displacement with 123I and 18F

Xiao‐Shu ‐S He, Dale O. Kiesewetter, Kan Sam Lee, Mariena V. Mattson, D. R. Weinberger, Brian R. de Costa

Research output: Contribution to journalArticle

Abstract

Unlabelled and labelled 4‐fluoro‐ and 4‐iodo‐1‐[1‐(3‐hydroxyphenyl)cyclohexyl]piperidines (3 and 4, respectively), derivatives of phencyclidine, were synthesized in 3‐steps via nucleophilic displacement reaction of 1‐[1‐(3‐hydroxyphenyl) cyclohexyl]‐4‐(methanesulfonyloxy)piperidine (8). The displacement reaction with 3 molar equivalents of Bu4N+I gave 58% of 4 with no detectable methanesulfonate elimination. Reaction of a large excess of 8 with Na123I under similar conditions gave up to 40% yield of [123I]8. In contrast reaction of 8 with 3 molar equivalents of unlabelled Bu4N+F in refluxing acetonitrile yielded only 3.1% of 3 and 97% of elimination product. Similarly, reaction of a large excess of 8 with Bu4N+18F at 80 °C in acetonitrile failed to yield detectable quantities of [18F]3. However, low (0‐4%) yields of [18F]3 were obtained using 18F in the presence of varying proportions of inorganic base and Krytofix in acetonitrile.

Original languageEnglish (US)
Pages (from-to)573-581
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume33
Issue number7
DOIs
StatePublished - Jul 1993
Externally publishedYes

Keywords

  • 1‐[1‐(3‐hydroxyphenyl)cyclohexyl]‐4‐(methanesulfonyloxy) piperidine (8)
  • 4‐fluoro‐ and 4‐iodo‐1‐[1‐(3‐hydroxyphenyl)cyclohexyl] piperidines
  • BuNF
  • BuNFNaI
  • BuNI
  • Kryptofix
  • elimination
  • nucleophilic displacement
  • phencyclidine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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