Hydrochloric Acid → Benzyl piperazine-1-carboxylate

Participants

Reaction Steps

A mixture of 17.2 g (0.2 mole) of anhydrous piperazine, 40 ml of water and 60 ml (0.36 mole) of 6N hydrochloric acid in 300 ml of methanol was heated to boiling. Small portions of benzylchloroformate (total 48 g, 0.28 mole) and 4N sodium hydroxide (total 100 ml) were added alternately to maintain a pH of 4.5-5.5. The mixture was heated under reflux for 3 hr, allowed to cool overnight, concentrated in vacuo to remove the methanol, made alkaline with sodium hydroxide and extracted with dichloromethane. The dichloromethane extract was washed with water and then extracted with 400 ml of 1N hydrochloric acid. The acid extract was washed with dichloromethane, made alkaline with sodium hydroxide, and extracted with dichloromethane. The dichloromethane extract was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness in vacuo to give 25 g of crude product. Distillation under vacuum afforded 21.3 g (48%) of the product, bp 140°-143° (0.1 torr). VPC indicated the material consisted of 97% of a single component and the NMR was consistent with the assigned structure.

Provenance & Evidence