Diallylamine → 3-(Cyanoimino)-3-(N,N-diallylamino)propionitrile

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Reaction Steps

A solution of 4.00 g (0.0292 m) ethyl N,2-dicyanoacetimidate and 2.83 g (0.0292 m) diallylamine in 60 ml tetrahydrofuran is stirred at 0° C. for twelve hours. The reaction is concentrated and filtered through silica gel (2% MeOH/CH2Cl2 eluent). The organic phase is concentrated and the residue chromatographed (HPLC, 1"× 40" of 30-50 μ silica gel, 2% MeOH/CH2Cl2) to give product. A minor impurity (200 mg) crystallizes out from CH2Cl2 -C6H12. The residual oil (3.08 g, 56%) has nmr, ir, and mass spec which are consistent.

Provenance & Evidence