l,4-Bis(2-chioroethyl)-l,4-Diazabicyclo[2.2.1]heptane Diperchlorate

Reaction between bis(2-chloroethyl)amine and formalin in ethanol solution was found to yield l,4-bis(2-chloroethyl)-l,4-diazabicyclo[2.2.1]heptane (la) dichloride, a novel quaternary ammonium salt. The condensation leading to diazabicyclo[2.2.1]heptane la was found generally useful and substances lb-1f were easily obtained. Hydrogenolysis of, for example, salt le was found to yield piperazine 8b. Other pertinent aspects of the chemical and physical (principally proton magnetic resonance) evidence in support of the new ring system have been summarized.