13114-22-2Relevant articles and documents
4,4′-Trimethylenedipiperidine, a safe and greener alternative for piperidine, catalyzed the synthesis of N-methyl imines
Gorjian, Hayedeh,Khaligh, Nader Ghaffari
, (2022/02/21)
A practical and facile synthesis of various N-methyl imines, versatile scaffolds, was conducted at 85?°C using 4,4′-trimethylenedipiperidine as a safe and green catalyst. This reagent is a commercially available solid and can be handled easily. It has high thermal stability, low toxicity, and good solubility in green solvents such as water and ethanol. The regenerated catalyst demonstrated stable activity after several recycle runs, and any changes were detected in its chemical structure by 1H NMR monitoring. The novelty of the current work is that the 4,4′-trimethylenedipiperidine can act as a promising alternative for piperidine in organic reaction at higher temperatures due to its broad liquid range temperature, thermal stability, acceptor/donor hydrogen bond property, and other unique merits. Furthermore, the current protocol avoids waste generation in the workup process, which is a drawback in most previous reported procedures.
Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
Chen, Dongping,Li, Kaidi,Tang, Wenjun,Xu, Guangqing,Xu, Ronghua,Zhou, Mingkang
supporting information, p. 10337 - 10342 (2020/07/04)
We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.
Mechanosynthesis of N-methyl imines using recyclable imidazole-based acid-scavenger: In situ formed ionic liquid as catalyst and dehydrating agent
Khaligh, Nader Ghaffari,Ling, Ong Chiu,Mihankhah, Taraneh,Johan, Mohd Rafie,Ching, Juan Joon
, p. 194 - 199 (2018/12/04)
1,1′-(1,4-Butanediyl)bis(imidazole) was prepared by a modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional condensation reaction with ecological benefits and convenience of a facile mechanosynthetic process. The current method has advantages such as reduced waste by avoiding solvent, exclusion of hazardous materials during the reaction, elimination of handling an anhydrous gas in an evacuated container or a solution of methylamine in ethanol, good yields for relatively unreactive benzaldehydes containing electron-donating substituents, short reaction times, and metal- and acid-free conditions. Furthermore, the promoter was easily regenerated and reused several times with no significant loss of activity.