Synthesis
General procedure for the synthesis of tris(3-aminopropyl)amine from 3,3',3''-hypromellitic acid tripropionitrile: 17.6 g of tris(3-nitropropyl)amine, 7.5 g of NaOH, 25 mL of hydrazine hydrate and 100 mL of ethanol were added to a three-necked round-bottomed flask at 0 °C, and 5.0 g of Raney Ni was added slowly.The progress of the reaction was monitored during the course of the reaction by thin layer chromatography (TLC). The progress of the reaction was monitored by thin layer chromatography (TLC) during the reaction. Upon completion of the reaction, the reaction mixture was recovered by filtration, pH was adjusted to 1-12 and left to stand to separate the salt. Subsequently, the obtained clarified yellow liquid was vacuum distilled to collect the fraction at 120-125°C. The yield was 92%. The product was characterized by 1H NMR (CDCl3) and IR spectroscopy: 1H NMR (CDCl3): δ 1.42 (d, 6H); 2.45 (t, J=5.8Hz, 6H); 1.58 (tt, J=5.8Hz, 5.6Hz, 6H); 2.70 (t, J=5.6Hz, 6H). ir (cm-1): 3346. 3288, 2862, 1575, 1471, 1315, 819.
References
[1] Materials Research Bulletin, 2014, vol. 56, p. 12 - 18
[2] Angewandte Chemie, 1993, vol. 105, # 9, p. 1367 - 1370
[3] Journal of the American Chemical Society, 1945, vol. 67, p. 1995
[4] Helvetica Chimica Acta, 1979, vol. 62, p. 2763 - 2787
[5] Journal of the American Chemical Society, 1989, vol. 111, # 1, p. 186 - 190
