1555-58-4Relevant articles and documents
An efficient synthesis of N,N,N′,N′,N″-pentamethyldipropylenetriamine
Gui, Sizhe,Mu, Manman,Luo, Hao,Liu, Na,Shen, Huawei,Chen, Ligong
, p. 486 - 488 (2016/08/13)
N,N,N′,N′,N″-Pentamethyldipropylenetriamine (PMDPTA) has for a long time been employed as an efficient catalyst in the production of polyurethane materials. A green and effective synthetic route to PMDPTA was successfully established from experiments described in this paper. PMDPTA was obtained from methylamine, acrylonitrile and formaldehyde via a Michael addition, catalytic hydrogenation and methylation in 65% overall yield. Furthermore, methanol was employed as the only solvent in all of the three steps, resulting in the convenient recovery of methanol. This route is thus suitable for industrial production.
Chemistry of Nitrogen Mustard studied by Nuclear Magnetic Resonance Spectroscopy
Golding, Bernard T.,Kebbell, Michael J.,Lockhart, Ian M.
, p. 705 - 714 (2007/10/02)
Reactions of the nitrogen mustard drug 2-chloro-N-(2-chloroethyl)-N-methylethanamine with nucleophiles in aqueous solution have been studied by 1H and 13C n.m.r. spectroscopy.Conditions have been devised for converting the mustard into the N-2-chloroethyl-N-methylaziridinium ion which has been characterized by 1H n.m.r. spectroscopy.To assist the studies of reactions of the mustard by 13C n.m.r. spectroscopy, it has been prepared labelled at both C-2 atoms by 13C.It is shown that reactions of the mustard with strong nucleophiles (e.g. thiosulphate) proceed to a product of disubstitution, without the aziridinium ion being detected spectroscopically, although its intermediacy is inferred by examining the distribution of 13C in product from 13C-labelled mustard.Less reactive nucleophiles (e.g. thiourea) yield a product of disubstitution via spectroscopically detected intermediates (aziridinium ion and monosubstituted intermediate).Relatively weak nucleophiles (e.g. guanosine) did not give detectable products of substitution; cis- and trans-NN'-2-chloroethyl-NN'-methylpiperazinium dichloride were formed via the aziridinium ion.The reaction of the mustard with excess of ammonia gives a 3 : 2 ratio of 2-amino-N-(2-aminoethyl)-N-methylethanamine and N-methylpiperazine.The distribution of 13C label in these products derived from 13C-labelled drug shows that the triamine is formed via aziridinium intermediates, whilst the piperazine arises via intramolecular cyclisation of the intermediate 2-amino-N-(2-chloroethyl)-N-methylethanamine.
