Compound can be prepared in several related ways: 1) The condensation of N-(1-phenylisopropyl)methylamine (I) with 1,2-dibromopropene (A) by heating at 100 C gives N-(1-phenylisopropyl)-N-methyl-2-bromopropenylamine (II), which is then dehydrobrominated and isomerized by treating with KOH in refluxing ethanol water. 2) By heating a mixture of (I) and propargyl bromide (B) at 100 C. 3) By reductocondensation of (I) with propargyl aldehyde (C) by means of amalgamated Al in ethanol. 4) By condensation of (I) with formaldehyde and acetylene by means of CuCl in hot dioxane. 5) By condensation of 1-phenylisopropyl chloride (III) with N-methylpropargylamine (IV) by heating at 80 C in a sealed tube.
The reduction of 11C-CO2 (I) by means of LiAlH4 in THF gives 11C-methanol (II), which is treated with 57 % IH to yield 11C-methyl iodide (III). The reaction of (III) with silver triflate affords 11C-methyl triflate (IV). Finally, (R)(-)-nor-selegiline (nor-deprenil) (V) is methylated with the radiolabeled methyl triflate (IV) by means of NaOH in aqueous acetone to obtain the target radiolabeled compound.