1864-93-3Relevant articles and documents
Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles
Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.
, p. 1235 - 1240 (2018/02/09)
N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.
Catalyst-free one-pot reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids using sodium borohydride in 2,2,2-trifluoroethanol
Tajbakhsh, Mahmood,Hosseinzadeh, Rahman,Alinezhad, Heshmatollah,Ghahari, Somayeh,Heydari, Akbar,Khaksar, Samad
experimental part, p. 490 - 496 (2011/03/20)
A simple and convenient procedure for the reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids is described using sodium borohydride as a reducing agent in 2,2,2- trifluoroethanol without use of a catalyst or any other additive. The solvent can be readily recovered from reaction products in excellent purity for direct reuse. Georg Thieme Verlag Stuttgart - New York.
Addition of NN-Dimethylaniline Oxides to Nitrilium Salts and to Dimethyl Acetylenedicarboxylate. Direct Alkylamination of NN-Dimethylanilines
Sheradsky, Tuvia,Nov, Eliahu
, p. 527 - 530 (2007/10/02)
NN-Dimethylaniline oxide (1) and its ring-substituted derivatives react with N-alkylacetonitrilium salts to give the corresponding 2- and 4-(N-alkylacetamido)dimethylanilines.The mechanism, Which involves migration of an amide group from the aniline nitrogen onto the ring, is discussed.Addition of the oxide (1) to dimethyl acetylenedicarboxylate leads either to demethylation of the aniline (main path in dichloromethane) or to a rearrengement, which involves migration of the succinyl moiety onto the ortho-carbon (in ethanol).
