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Synthesis of [ 14 C]‐pargyline {N‐methyl‐N‐([1‐ 14 C]‐propargyl)benzylamine} with the radioactive label on the propargyl group
Author(s) -
Goon David J. W.,
Elberling James A.,
Demaster E. G.,
Nagasawa Herbert T.
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580280211
Subject(s) - chemistry , benzylamine , methylene , propargyl , methylamine , formaldehyde , pargyline , yield (engineering) , medicinal chemistry , solvent , methanol , aqueous solution , methyl group , organic chemistry , nuclear chemistry , group (periodic table) , catalysis , materials science , monoamine oxidase , metallurgy , enzyme
A one‐pot reaction scheme leading to 14 C‐labeled pargyline (N‐methyl‐N‐ propargylbenzylamine) where in the radioactive label from [ 14 C]‐formaldehyde is synthetically incorporated into the methylene group of the propargyl side chain is described. Thus, [ 14 C]‐formaldehyde (aqueous solution) is condensed in solvent dioxane with N‐methyl‐benzylamine and mono ‐trimethylsilylacetylene in the presence of cupric acetate dihydrate at elevated temperatures (85–86°) for 24 hrs. The Mannich condensation product is then desilylated and the radiolabeled pargyline is purified by partitioning in ether from acid and base followed by flash chromatography, and isolated as the hydrochloride. The radioactive yield is 58%. This method should be generally applicable for the incorporation of radioactive label into the propargyl methylene group of other drugs containing a propargyl side chain.