2591-84-6

Usage

InChI:InChI=1/C7H13NO/c1-7-3-2-4-8(5-7)6-9/h6-7H,2-5H2,1H3

Upstream product

• 626-56-2 3-Methylpiperidine 
• 109-94-4 formic acid ethyl ester 
• 50-00-0 formaldehyd 
• 18513-83-2 3-methyl-1-(2-methyl-propenyl)-piperidine 
• 67990-20-9 1,2-bis(3-methylpiperidin-1-yl)ethane 
• 201230-82-2 carbon monoxide 
• 302-17-0 chloral hydrate 
• 96-26-4 dihydroxyacetone 
• 124-38-9 carbon dioxide 

Downstream Products

• 637751-93-0 3-(2,3-dihydrobenzo[1,4]dioxan-6-yl)-7-hydroxy-8-(3-methylpiperidin-1-ylmethyl)-chromen-4-one 

Relevant academic research and scientific papers

Rutheniumcluster als Katalysatoren fuer die Carbonylierung von cyclischen Aminen

The tri- and tetra-nuclear ruthenium clusters Ru3(CO)12, - and - have been found to catalyse the carbonylation of cyclic amines such as piperidine, 3-methylpiperidine, pyrrolidine, heptamethylene imine, morpholine and piperazine to give the corresponding formamides.The catalytic reaction works with only carbon monoxide or a mixture of carbon dioxide and hydrogen.In the case of the neutral catalyst precursor, carbamoyl clusters of the type (μ2-H)Ru3(CO)10(μ2,η2-OCNR2) have been isolated from the reaction mixture.

The synthesis of cyanoformamides via a CsF-promoted decyanation/oxidation cascade of 2-dialkylamino-malononitriles

A mild and efficient method for the synthesis of cyanoformamides from N,N-disubstituted aminomalononitriles with CsF as the promoter has been developed. This method features a wide substrate scope and high reaction efficiency, and will facilitate corresponding cyanoformamide-based biological studies and synthetic methodology development.

Selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes and methylamines from cyclic amines and CO2/H2 catalyzed by an ionic liquid-Pd/C system

The reduction of CO2 with amines and H2 generally produces N-formylated or N-methylated compounds over different catalysts. Herein, we report the selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes, and methylamines, which is achieved over an ionic liquid (IL, e.g., 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIm][BF4])-Pd/C catalytic system. By simply varying the reaction temperature, formamides and methylamines can be selectively produced, respectively, in high yields. Interestingly, 1,2-bis(N-heterocyclic)ethanes can also be obtained via the McMurry reaction of the formed formamide coupled with subsequent hydrogenation. It was found that [BMIm][BF4] can react with formamide to form a [BMIm]+-formamide adduct; thus combined with Pd/C it can catalyze McMurry coupling of formamide in the presence of H2 to afford 1,2-bis(N-heterocyclic)ethane. Moreover, Pd/C-[BMIm][BF4] can further catalyze the hydrogenolysis of 1,2-bis(N-heterocyclic)ethane to access methylamine. [BMIm][BF4]-Pd/C was tolerant to a wide substrate scope, giving the corresponding formamides, 1,2-bis(N-heterocyclic)ethanes or methylamines in moderate to high yields. This work develops a new route to produce N-methylamine and opens the way to produce 1,2-bis(N-heterocyclic)ethane from cyclic amine as well.

Choline-based ionic liquids for CO2 capture and conversion

Choline-based ionic liquids (Ch-ILs) with anions possessing interacting sites to attract CO2 were designed, which could capture CO2 with capacity >1.0 mol CO2 per molar IL under ambient conditions. Moreover, this kind of ILs combining with CuCl could catalyze the formylation of amines with CO2/H2 at 120 °C. Especially, choline imidazolate showed the best performance, affording a series of N-formamides in excellent yields. It was demonstrated that the IL activated CO2 and the synergistic effect between the IL and CuCl resulted in the high activity for catalysing the formylation of amines with CO2/H2.

Method for preparing N-formylated amine compounds

The invention discloses a method for preparation N-formylated amine compounds. In the method, the amine compounds and 1,3-dihydroxy acetone are taken as reaction raw materials reacting in a reactor for 2-48 hours at the reaction temperature of 0-100DEG C in a reaction medium in the presence of composite catalysts and oxidants, and the N-formylated amine compounds are obtained. The method is simpleand moderate in reaction conditions, cost can be reduced, target products can be obtained with high yield, and the catalysts used have high catalytic activity and are easy to be separated from a reaction system and reuses; the method is environment friendly during the whole process, the reaction raw materials are easy to be converted from biodiesel by-product propylene glycol, and use of glycerolis facilitated.

Selective N-Formylation of Amines with H2 and CO2 Catalyzed by Cobalt Pincer Complexes

N-formylation of amines utilizing CO2 in the presence of reducing agents constitute an important methodology in organic synthesis. Presented herein is a selective N-formylation of amines with CO2 and H2 catalyzed by complexes of Earth-abundant cobalt. A wide range of amines were converted to their corresponding formamides under CO2 and H2 pressure, catalyzed by Co-PNP pincer complex, generating water as the sole byproduct.

Supported nano-gold-catalyzed N-formylation of amines with paraformaldehyde in water under ambient conditions

A simple and efficient Au/Al2O3 catalyst was prepared by the co-precipitation method for the oxidative N-formylation of amines with paraformaldehyde. Under the optimized reaction conditions, excellent amine conversion and N-formamide selectivity can be obtained with up to 97% yield with water as the solvent under ambient conditions. This catalyst tolerated a wide range of primary amines and second amines, and it can be reused for at least five runs without obvious deactivation.

Visible light induced photocatalytic conversion of enamines into amides

A series of enamines were photocatalytically cleaved to produce amide products under simple visible-light irradiation from a 45 W household light bulb. Mechanistically, the reactions appear to involve photosensitized formation of a singlet oxygen intermediate and a subsequent [2+2] cycloaddition event. Georg Thieme Verlag Stuttgart, New York.

Visible-light photo-catalytic C-C bond cleavages: Preparations of N,N-dialkylformamides from 1,2-vicinal diamines

A range of 1,2-vicinal diamines were smoothly converted into N,N-dialkylformamides under the synergistic actions of Ru(bpy) 3Cl2 photo-catalyst, 45 W household lighting bulb, and Cs2CO3 basic additive under very mild reaction conditions. The process involves visible light-enabled photo-catalytic cleavage of C-C bond as the strategic event.

KINETICS OF N-FORMYLATION OF PIPERIDINE AND RELATED COMPOUDS

The kinetics of the N-formylation of piperidine and 3-methylpiperidine with chloral hydrate and 1,2,3,4-tetrahydroisoquinoline with chloral in toluene, have been investigated.The reactions are first order in both reactants.The formylation of piperidine is faster than that of 1,2,3,4-tetrahydroisoquinoline and somewhat slower than that of 3-methylpiperidine.