4788-37-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 1673, 1972 DOI: 10.1021/jo00975a049

InChI:InChI=1/C10H15N/c1-3-11(2)9-10-7-5-4-6-8-10/h4-8H,3,9H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 14321-27-8 N-ethylbenzylamine 
• 100-44-7 benzyl chloride 
• 75-31-0 isopropylamine 
• 124-38-9 carbon dioxide 
• 100-52-7 benzaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 103-67-3 benzyl-methyl-amine 
• 147227-64-3 N-(Benzotriazol-1-yl-phenyl-methyl)-N-methyl-acetamide 
• 75-03-6 ethyl iodide 
• 5817-70-9 methyl N-benzylcarbamate 
• 141-78-6 ethyl acetate 
• 624-78-2 N-Ethylmethylamine 

Downstream Products

• 4217-54-3 9,10-dihydro-10-methylacridine 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 14321-27-8 N-ethylbenzylamine 
• 82862-59-7 benzyl(ethyl)methylamine*BFCl₂ 
• 82862-58-6 benzyl(ethyl)methylamine*BF₂Cl 
• 82862-57-5 benzyl(ethyl)methylamine*BF₃ 
• 82862-60-0 benzyl(ethyl)methylamine*BFBr₂ 

Relevant academic research and scientific papers

Silicon hydrogenation reaction method of organic boron and inorganic alkali catalysis amide (by machine translation)

The method is characterized in that organic boron and inorganic bases are used as catalysts, silane is used as a reducing agent, primary amide is reduced to primary amine or dehydration dinitrile, the secondary amide is reduced to a secondary amine or aldimine, and the tertiary amide is reduced to tertiary amine. The method has the advantages of simple operation, mild reaction conditions, wide substrate universality, good functional group compatibility and the like, and has the characteristics of good stability, cheap and accessible catalyst, simple and convenient operation, high practicality and the like. (by machine translation)

UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source

We demonstrate the first metal-organic framework (MOF) that catalyzes N-methylation of amines using 1 atm CO2 and phenylsilane under ambient conditions. Compared with its homogeneous analog, the incorporation of N-heterocyclic carbene (NHC) into the MOF provides more efficient catalysis with improved reaction kinetics, turnover numbers and recyclability. Moreover, the metalated NHC functionalized MOF achieves direct N-methylation of amines bearing carboxylate moieties, which are common building blocks in pharmaceutical chemistry.

Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2

Functionalization of amines by using CO2 is of fundamental importance considering the abundance of amines and CO2. In this context, the catalytic formylation and methylation of amines represent convenient and successful protocols for selective CO2 utilization as a C1 building block. This study represents the first example of selective catalytic double N-formylation of aryl amines by using a dinuclear Mn complex in the presence of phenylsilane. This robust system also allows for selective formylation and methylation of amines under a range of conditions.

A general catalytic methylation of amines using carbon dioxide

Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright

Palladium nanoparticle catalysts in ionic liquids: Synthesis, characterisation and selective partial hydrogenation of alkynes to Z-alkenes

The simple heating (120 °C) of Pd(OAc)2 in 1-butyronitrile-3-methylimidazolium-N-bis(trifluoromethane sulfonyl)imide ((BCN)MI·NTf2) under reduced pressure leads to the formation of stable and small-sized Pd(0)-NPs (diameter: 7.3 ± 2.2 nm). These metal nanoparticles were characterised by means of TEM, HRTEM and XPS analysis techniques. Moreover, the potential for partial hydrogenation of alkynes in multiphase systems was evaluated. The hydrogenation of internal alkynes at 25 °C and under 1 bar of hydrogen yields Z-alkenes (up to 98% selectivity). Application of higher hydrogen pressure (4 bar) in these reactions always led to the formation of alkanes without the detection of any alkenes. TOF values were attained up to 1282 h-1 with a good recyclability of the system which does not lose its activity for at least 4 runs. The Royal Society of Chemistry 2011.

Efficient synthesis of tertiary amines from secondary amines

Reliable N-alkylations of secondary amines have been developed. By using DIAD and TPP (or PS-TPP) a variety of secondary amines can be converted to the corresponding tertiary amines in good to excellent yields with diverse alkylhalides; no formation of quaternary amine salts are observed. These protocols are amenable to combinatorial chemistry libraries, and are also useful for the syntheses of secondary amines by an acid lysis of the cleavable tertiary amino resins.

The Conversion of Secondary into Tertiary Amides Using Benzotriazole Methodology

N-Alkyl-N-amides, easily prepared from benzotriazole, an aldehyde, and a secondary amide, react readily with organozinc reagents to give tertiary amides in moderate to good yields.They are also reduced by LiAlH4 to afford tertiary amines.

Mixed Boron Trihalide Adducts of Amines: A Multinuclear Nuclear Magnetic Resonance Study

The (19)F chemical shifts of mixed boron trihalide adducts of tertiary amines have a marked dependence on the steric effects of amine substituents, as estimated from the 'cone angle' of the amines.Base strength of the amine has little effect on adduct (19)F shifts, but does have a pronounced effect on the rate of halogen redistribution.The (11)B and (13)Cchemical shifts and (11)B-(19)F coupling constants of the adducts are discussed.Amines NRR'R'' become chiral when complexed to Lewis acids, since complexation stops the rapid inversion process.Because of this the fluorines in R''R'RN*BF2X (X=Cl, Br, or I) adducts are diastereotopic and magnetically non-equivalent, differing in chemical shift by up to 2 p.p.m.The four-adduct system of benzyl(ethyl)methylamine with BF(n)I(3-n)(n=0-3) gives rise to the cation B(PhCH2NMeEt)2F2(1+) which, because of the chirality of the co-ordinated amines, exists in meso and optically active forms distinguishable by (19)F n.m.r. spectroscopy.

Reaction of Ortho Esters with Secondary Amines

The scope of the reaction of ortho esters with secondary amines has been explored.With p-toluenesulfonic acid as catalyst, N-alkylanilines and orthoformates gave high yields of N-alkylformanilides and N,N-dialkylanilines in contrast to previous work with other acid catalysts where ortho amides were produced in low yield.Aliphatic cyclic amines (e.g., morpholine, piperidine) and orthoformates gave the corresponding ortho amides.This constitutes a new convenient synthesis of these useful reagents.

Preparation of esters of phosphorus acids

Esters of phosphorus acids are prepared by an improved process whereby aromatic alcohols and phosphorus halides are reacted at specified temperatures in the presence of amine catalysts thereby providing high yields of substantially pure esters and allowing preparation of selected halogen-containing mono- and di-esters of phosphorus acids wherein halogen is directly bonded to phosphorus having substantially no side reactant contamination. The phosphorus esters are useful as intermediates in the preparation of plasticizers, oil additives and functional fluids.