17635-38-0Relevant academic research and scientific papers
Acyclic Tertiary Amines as Nucleophiles in Substitution Reactions of Aromatic and Heteroaromatic Halides
Matsumoto, Kiyoshi,Hashimoto, Shiro,Otani, Shinichi
, p. 306 - 307 (1991)
Even acyclic tertiary amines such as triethylamine, tri-n-propylamine and tri-n-butylamine, which have been believed to be inert to aromatic and heteroaromatic halides, underwent SNAr reactions with aromatic and heteroaromatic halides to give the dialkylamino derivatives; in the case of monocyclic amines like N-methylpyrrolidine and N-methylpiperidine, the dealkylation being regioselective.
Ruthenium complex-controlled catalytic N-mono- or N,N-dialkylation of heteroaromatic amines with alcohols
Watanabe, Yoshihisa,Morisaki, Yasuhiro,Kondo, Teruyuki,Mitsudo, Take-Aki
, p. 4214 - 4218 (2007/10/03)
Heteroaromatic amines were N-alkylated with primary alcohols at 150-200°C in the presence of a catalytic amount of various ruthenium complexes to give the corresponding monoalkylated and dialkylated amines in good to high yields. For example, 2-aminopyridine reacted with an excess of ethanol at 180°C for 20 h in the presence of dichlorotris(triphenylphosphine)ruthenium [RuCl2-(PPh3)3] to give 2-(ethylamino)pyridine (1) and 2-(diethylamino)pyridine (2) in 9% and 70% yields, respectively. On the other hand, when (η4-1,5-cyclooctadiene)(η 6-1,3,5-cyclooctatriene)ruthenium [Ru(cod)(cot)] was used as a catalyst, even in the presence of excess ethanol, 1 was obtained in 85% yield with high selectivity. The addition of tertiary phosphines and phosphites to Ru(cod)-(cot) increased the yield of the dialkylated amine.
