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A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids
ABX Advanced Biochemical Compounds, Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany
Department of Nuclear Medicine, Klinikum rechts der Isar, Technische Universität München, Ismaninger Strasse 22, D-81675 Munich, Germany
Present Address: Department of Chemistry and Food Chemistry, Organic Chemistry I, Dresden University of Technology, Bergstrasse 66, D-01069 Dresden, Germany.
Present Address: Scintomics Up North AS, Utveien 15, N-1430 As, Norway.
* Author to whom correspondence should be addressed.
Received: 3 January 2012; in revised form: 20 February 2012 / Accepted: 24 February 2012 / Published: 7 March 2012
Abstract: The route selection and development of a convenient synthesis of 4-carboxy-4-anilidopiperidines is described. Previous routes were hampered by the low yield of the target esters as well as the inability to convert the esters to the required free acids. Considerations for large-scale production led to a modified synthesis that utilised a tert-butyl ester of 4-carboxy-4-anilidopiperidines which resulted in a dramatic increase in the overall yield of the target N-propionylated- 4-anilidopiperidine-4-carboxylic acids and their corresponding methyl esters. These compounds are now available for use as precursors and reference standards, of particular value for the production of 11C and 18F-labelled 4-carboxy-4-anilidopiperidine radiotracers.
Keywords: 4-anilidopiperidines; tert-butyl ester; opioid receptors; positron emission tomography
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Marton, J.; Glaenzel, B.; Roessler, J.; Golaszewski, D.; Henriksen, G. A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids. Molecules 2012, 17, 2823-2832.
Marton J, Glaenzel B, Roessler J, Golaszewski D, Henriksen G. A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids. Molecules. 2012; 17(3):2823-2832.
Marton, János; Glaenzel, Brita; Roessler, Julia; Golaszewski, Daniela; Henriksen, Gjermund. 2012. "A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids." Molecules 17, no. 3: 2823-2832.