13.6 grams of chloroacetyl guanide is added while stirring to a solution of
22.6 grams of heptamethylene imine in 200 ml of benzene. After warming for
1 hour, and then cooling, the solution is filtered and the filtrate concentrated
under reduced pressure. The residue, containing the 2-(1-N,N-heptamethylene-imino)-aceticacid guanide, is suspended in tetrahydrofuran
and added to a refluxing solution of 6 grams of lithium aluminum hydride in
tetrahydrofuran. After completion of the reaction, the excess of lithium
aluminum hydride is decomposed by adding water, then aqueous sodium
hydroxide. The solid material is filtered off, the filtrate is acidified with sulfuric
acid and the 2-(1-N,N-heptamethylene-imino)-ethyl-guanidine sulfate can be
recovered and recrystallized from aqueous ethanol, MP 276° to 281°C (with
decomposition).
