[C:1](#[N:4])[CH:2]=[CH2:3].[OH:5][CH2:6][CH2:7][NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1.N.[H][H]>[Ni].C(O)C>[NH2:4][CH2:1][CH2:2][CH2:3][NH:17][CH2:16][CH:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH:8][CH2:7][CH2:6][OH:5])[CH2:11][CH2:12]1
Acrylonitrile (10.6 g., 0.2 mole) is added dropwise over a 15 minute period to N-(2-hydroxyethyl)-1,4-cyclohexanebis(methylamine) (37.2 g., 0.4 mole) with stirring and ice bath cooling. After complete addition, the reaction mixture is stirred an additional 2 hours at 5° C., allowed to gradually warm over a 1 hour period. heated 2 hours at 45° C. and finally 1 hour at 90° C. It is then fractionated under reduced pressure up to an internal temperature of 170° C. The residue is dissolved in 200 ml. ethyl alcohol, cooled in an ice bath and saturated with ammonia gas at 0° C. Approximately 5 ml. of sponge nickel catalyst (W. R. Grace Co., Davison Chem. Division) is added and the mixture shaken under hydrogen at 150 psi until no further hydrogen uptake. The catalyst is removed by suction, filtration under nitrogen, the solvent stripped away and the residue fractionally distilled under reduced pressure. The trimaine product is readily distinguished from cyanoethylated diamine by its lower Rf on silica gel using a solution of 1 volume concentrated aqueous ammonium hydroxide in 4 volume methyl alcohol. The synthesis is an adaptation of the method of M. Israel et al, J. Med. Chem., 7, 710 (1964) for the preparation of polymethylenepolyamines.
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