1932-04-3

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C12H24N2/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H2/p+2

Upstream product

• 110-89-4 piperidine 
• 106-93-4 ethylene dibromide 
• 626-67-5 N-methylcyclohexylamine 
• 107-21-1 ethylene glycol 
• 1932-03-2 2-(piperidin-4-yl)ethyl chloride 
• 151257-52-2 1-[2-(1H-1,2,3-benzotriazol-1-yl)-1,2-bis(piperidin-1-yl)ethyl]-1H-1,2,3-benzotriazole 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 7732-18-5 water 
• 1676-62-6 dispiro-N,N'-dipiperidinopiperazinium dichloride 
• 107-06-2 1,2-dichloro-ethane 
• 124-38-9 carbon dioxide 
• 2591-86-8 N-Formylpiperidine 
• 110-86-1 pyridine 

Downstream Products

• 92326-19-7 1,4-Di(N,N-pentamethylen)-piperazinium-dibromid 
• 68601-52-5 1,2-Di-(N-piperidyl)ethan-bis-N-oxid 
• 148696-20-2 [Pd(phenoxo)2(1,2-dipiperidinoethane)] 
• 871656-23-4 iodo(phenyl)(1,2-dipiperidinoethane)palldium(II) 
• 1247050-79-8 [Ni(2,6-dimethyl-3,5-heptanedionate)(1,2-dipiperidinoethane)]BPh₄ 
• 1247050-76-5 [Ni(3,5-heptanedionate)(1,2-dipiperidinoethane)]BPh₄ 
• 148661-16-9 [Pd(pentafluorophenolato)2(1,2-dipiperidinoethane)] 
• 2591-86-8 N-Formylpiperidine 

Relevant academic research and scientific papers

Crystal structure of a butyllithium 1,2-dipiperidinoethane dimer complex

The crystal structure of butyllithium solvated by 1,2-dipiperidinoethane, BuLi?DPE-6, which has been used as an initiator for a number of important commercial anionic polymerization reactions, is reported. The complex crystallizes from pentane as a centrosymmetric dimer in the monoclinic space group P21/n with a∈=∈9.8619(12), b∈=∈17.963(2), c∈=∈10.3655(12) A, β∈=∈114.090(2)° and Z∈=∈2. The dimer is located on a crystallographic inversion center. The crystal under investigation was found to be non-merohedrally twinned. In contrast to the two other dimeric BuLi complexes previously structurally characterized in the solid state, BuLi?DPE-6 has a planar central Li 2C2 core. Semi-empirical (PM3) calculations were used to determine the lowest energy conformations of the dimer and also identified three structural motifs that affect Li2C2 dimer ring planarity. Springer Science+Business Media, LLC 2007.

Synthesis of diverse well-defined functional polymers based on hydrozirconation and subsequent anti-Markovnikov halogenation of 1,2-polybutadiene

For the first time, hydrozirconation and halogenolysis of 1,2-polybutadiene (1,2-PBD, by living anionic polymerization) were studied to synthesize reactive polyhalohydrocarbons, which provide a platform for preparing well-defined functional polymers via macromolecular substitution. Hydrozirconation and halogenolysis afforded quite convenience for anti-Markovnikov hydrohalogenation of 1,2-PBD with controllable degree of functionalization. Diverse functional polymers and branched polymers were synthesized after macromolecular substitution reaction with a broad range of commercially available nucleophiles (amines, phenols, alcohols, carbanions, carboxylates, and azide) or macromolecular nucleophiles. NMR and GPC characterizations confirmed high conversion in substitution reaction and narrow molecular weight distribution of the resultant functional polymers, respectively. The methodology utilizing Schwartz's reagent for hydrozirconation of macromolecules could greatly facilitate the modification of vinyl groups containing polymers with high efficiency.

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.

Synthesis of Al-MTW with low Si/Al ratios by combining organic and inorganic structure directing agents

A rationalized combination of alkali cations and bulky dicationic organic structure directing agents (OSDAs) has allowed the synthesis of the Al-rich MTW zeolites with Si/Al ratios of ～12 and large pore accessibility. 27Al MAS NMR spectroscopy indicates that most of the aluminum atoms are in tetrahedral coordination in framework positions, and in situ infrared pyridine adsorption/desorption spectroscopy reveals strong Br?nsted acidity after cationic exchange for the Al-rich MTW. In addition, another MTW material with a Si/Al ratio of 30 has been synthesized under alkali-free conditions using a bulky dicationic molecule such as OSDA, the lowest Si/Al ratio being achieved for a MTW zeolite synthesized in the absence of alkali-cations in the synthesis media. The catalytic activity of these MTW materials has been tested for the n-decane cracking reaction, achieving higher catalytic activities and olefin yields than other related large pore zeolites.

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.

A study of 2-piperidino-1-ethanol and its derivatives as antimicrobial additives to oils

Some derivatives of 1-hydroxy-2-pyperidinoethane were studied as antimicrobial additives to lubricant oils.

Lewis Acid Complexed Heteroatom Carbanions; A New Concept for α-Metallation of Tertiary Amines

BF3 complexes of typical benzylic, allylic and saturated N-methyl tertiary amines were α-lithiated, with lithium tetramethylpiperidide (LTMP) or sec-butyllithium, and were treated with electrophiles.

A Novel Method for the Synthesis of Symmetrical Vicinal Tertiary and Secondary Diamines

A variety of symmetrical vicinal tertiary and secondary diamines are readily prepared in good to excellent yields by either Grignard reaction or reduction of the glyoxal bisproducts with benzotriazole and secondary or primary amines.

N-Alkylation d'amines en catalyse homogene. Synthese de mono- et de diamines cycliques

Ruthenium compounds are appropriate catalysts in the N-alkylation of amines.The synthesis of N-alkylated cyclic amines from a cyclic amine and an alcohol or via the condensation between a diol and a primary amine are described.The reaction with cyclic amines is highly selective, especially in the presence of a phosphine, making it a high yielding preparative procedure.The catalytic condensation between cyclic amines and diols yields either an aminoalcohol (A) or a bicyclic diamine (B).The temperature, the presence of phosphine, and the ratio of amine to diol are decisive in directing the reaction toward A or B.The proposed mechanism involves the dehydrogenation of the alcohol followed by attack of the amine on the aldehyde intermediate.