Chloroacetonitrile → 2-(4-Hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride

Participants

Reaction Steps

0.63 ml of chloroacetonitrile was added to a solution of 23 mg of metallic sodium in 4 ml of absolute methanol, and the mixture was stirred for about 30 minutes at room temperature. 1.5 g of 4-hydroxyiminopiperidine hydrochloride were then added and the stirring was continued for 2 hours, during which time a precipitate separated out. 25 ml of anhydrous ether were added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with ether, giving 2.22 g of 2-(4-hydroxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride.

Provenance & Evidence