Triethylamine → N-(1-Methyl-2-pyrrolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide

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Reaction Steps

To 1.74 g (0.01 mole) of phenyl isocyanide dichloride in dry Et2O with cooling under N2 is added 0.71 g (0.01 mole) of pyrrolidine followed by 1.01 g (0.01 mole) of Et3N with stirring. The mixture is allowed to stir for 11/2 hrs. and then filtered to remove precipitated Et3N.HCl. To the filtrate is added 1.96 g (0.02 mole) of 1-methyl-2-iminopyrrolidine in an ice-water bath. The resultant mixture is allowed to stir overnight under N2 and then filtered to remove N-methyl-2-iminopyrrolidine hydrochloride, m.p. 182°-188° C. The filtrate is evaporated to dryness in vacuo affording in an oil which is dissolved in MeOH (10 ml) and treated with an equimolar amount of L(+)-tartaric acid. The resultant solution is concentrated while adding i-PrOH to give crystals. Recrystallization from isopropanol-acetonitrile gives the pure L-(+)-tartrate salt, N-(1-methyl-2-pyrrolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide, m.p. 153°-56° C.

Provenance & Evidence