Ethylenediamine → 1-[1,5-Di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentyl]-1,4,8-triazaoctane

Participants

Reaction Steps

As an alternative to using an unsymmetrical amine V and obtaining a mixture of Schiff bases VI and VI(a) or VI(b), the reaction can be conducted stepwise. For example, 1,2-diaminoethane may be converted to a Schiff base with 1,5-di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentanone, catalytically reduced, then the remaining primary amino nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-[1,5-di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentyl]-1,4,8-triazaoctane.

Provenance & Evidence