Denton Travis T, Joyce Abigail S, Kiely Donald E
Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, University of Montana, Missoula, Montana 59812, USA.
J Org Chem. 2007 Jun 22;72(13):4997-5000. doi: 10.1021/jo070245v. Epub 2007 May 31.
An improved process for the preparation of N-alkylbis(3-aminopropyl)amines is described. These triamines are of interest as monomers for the condensation polymerization with esterified carbohydrate diacids (aldaric acids) to generate the corresponding poly(4-alkyl-4-azaheptamethylene aldaramides). The triamine synthesis is comprised of two efficient steps and requires no chromatographic purification. Bisconjugate addition of alkylamines to acrylonitrile followed by catalytic hydrogenation of the N-alkylbis(cyanoethyl)amines over Raney nickel yields the target N-alkylbis(3-aminopropyl)amines. Much less solvent was used in the bisconjugate addition step then previously reported, and in the second step, a relatively low-pressure catalytic hydrogenation (50 psi of hydrogen) was employed using Raney nickel as the catalyst in a 7 N methanolic ammonia solvent system to afford the N-alkylbis(3-aminopropyl)amines of high purity in nearly quantitative yield.
