Acrylonitrile → [1-(2-Cyanoethyl)-4-piperidinyl]methyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate

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Reaction Steps

4-Piperidinylmethyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate (0.180 g, 0.55 mmol) was dissolved in acetone (10 ml) and treated with acrylonitrile (0.040 ml; 0.61 mmol). The solution was heated at reflux (18 hours), cooled and evaporated in vacuo to an orange gum. The gum was purified by flash silica-gel chromatography with CHCl3 →2% MeOH/CHCl3 as eluant to yield the title compound as a colourless oil (0.035g; 17%) which was converted to the oxalate salt, mp 101°-103° C.

Provenance & Evidence