6308-94-7Relevant academic research and scientific papers
Process Development for the Rhodium-Catalyzed Reductive Amination in a Thermomorphic Multiphase System
Künnemann, Kai U.,Bianga, Jonas,Scheel, Ricarda,Seidensticker, Thomas,Dreimann, Jens M.,Vogt, Dieter
, p. 41 - 49 (2020/01/02)
For the first time, the successful application of the homogeneously catalyzed reductive amination in a thermomorphic multiphase system (TMS) and the first reported scale-up of this reaction into a continuous process, which recovers and recycles the homogeneous catalyst in flow, is presented. Herein, the model substrate 1-decanal reacts with the secondary amine diethylamine to form the corresponding product N,N-diethyldecylamine. A thermomorphic multiphase system (TMS) is established as a recycling strategy to recover and reuse the catalyst for the continuous process. After screening different solvents for the TMS and optimizing the reaction conditions in batch mode, the recycling of the rhodium catalyst was realized in a fully automated miniplant. Parameters influencing the stability of the process were identified and optimized to develop the continuous process. The process was operated in a steady state over 90 h with yields >90% of the desired product and low catalyst leaching 1%/h.
Joint Synthesis of Tertiary Unsymmetrical and Symmetrical Aliphatic Amines
Kozlov,Tereshko,Basalaeva,Tarasevich
, p. 1095 - 1098 (2007/10/03)
Tertiary unsymmetrical and symmetrical aliphatic amines were prepared by reaction of higher (C8-C16) and lower (C2-C4) aliphatic alcohols with nitriles containing the same number of carbon atoms as the lower aliphatic alcohols. Reaction conditions ensuring nearly quantitative yields of tertiary amines were determined.
Aminoborohydrides as Reducing Agents. 1. Sodium (Dimethylamino)- and (tert-Butylamino)borohydrides as Selective Reducing Agents
Hutchins, Robert O.,Learn, Keith,El-Telbany, Farag,Stercho, Yuriy P.
, p. 2438 - 2443 (2007/10/02)
Replacement of a hydride in borohydride by an electron-donating alkylamino group greatly enhances the reducing ability of the resulting reagents.Thus, sodium (dimethylamino)- and (tert-butylamino)borohydrides (1, NaDMAB, and 2, NaTBAB, respectively) not only reduce aldehydes and ketones to alcohols but also are effective for the conversion of esters to alcohols and primary amides to amines in good to excellent yields.Tertiary amides are reduced to alcohols (i.e., N,N-dimethylamides) or amines (i.e.N,N-diisopropylamides) depending on the steric bulk of the alkyl substituents on nitrogen.However, secondary amides are not reduced by the reagents allowing selective conversion of primary and tertiary amides in the presence of secondary amides.Nitriles are attacked by the reagents but do not afford synthetically useful amounts of amine products.Aryl halides are slowly converted to arenes, but alkyl halides and epoxides undergo unusual reactions with the amino portion of the reagents.
