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Synthesis of [14C]-pargyline {N-methyl-N-([1-14C]-propargyl)benzylamine} with the radioactive label on the propargyl group

✍ Scribed by David J. W. Goon; James A. Elberling; E. G. Demaster; Herbert T. Nagasawa

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
245 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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