22014-89-7

Upstream product

• 107-10-8 propylamine 
• 100-39-0 benzyl bromide 
• 802294-64-0 propionic acid 
• 103-49-1 dibenzylamine 
• 123-38-6 propionaldehyde 
• 50-00-0 formaldehyd 
• 75-03-6 ethyl iodide 
• 22014-91-1 3-(dibenzylamino)prop-1-ene 
• 60479-65-4 (S)-2-(N,N-dibenzylamino)-1-propanol 
• 100-52-7 benzaldehyde 
• 108-03-2 1-Nitropropane 
• 35929-26-1 N,N-bis(phenylmethyl)-propionamide 
• 139-45-7 glyceryl tripropanoate 
• 780-25-6 N-benzylidene benzylamine 

Downstream Products

• 265669-75-8 tert-Butyl 3-(N-propyl-N-benzylamino)butanoate 
• 2032-33-9 N-benzyl-N-propylamine 
• 1374146-66-3 C₃₄H₄₀N₂ 

Relevant academic research and scientific papers

Direct Reductive Amination of Carbonyl Compounds with H2 Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N-Alkylation with Alkyl Halides

A general continuous-flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C?N bonds without production of any hazardous chemical waste. Applications to the synthesis of key intermediates toward active pharmaceutical ingredients (Donepezil and Arformoterol/Tamsulosin) are also described. (Figure presented.).

Efficient and Selective Hydrosilylation of Secondary and Tertiary Amides Catalyzed by an Iridium(III) Metallacycle: Development and Mechanistic Investigation

Readily accessible cationic IrIII metallacycles catalyze efficiently the chemoselective hydrosilylation of tertiary and secondary amides to amines. The catalyst described herein operates at low loadings using inexpensive 1,1,3,3-tetramethyldisiloxane and allows fast reactions with high yields, selectivities, and turnover numbers. A transient iminium intermediate has been observed for the first time by using mass spectrometry, and the activation of the catalyst and the silane reagent have been studied by using DFT calculations. These fundamental insights support the present and future improvements of IrIII metallacycles through proper ligand modifications and enable further broad applications of catalysts based on metallacycles.

Novel synthesis of N-alkyl amines from tandem coupling of either methylamine or nitroalkane with aldehyde

A novel tandem strategy for coupling of either methylamine or nitroalkane with aldehyde has been developed. This is the first demonstration that methylamine or nitroalkane is used as a methylation reagent, fabricating N-alkyl amines. The active Pt NWs allow for the selective preparation of a series of N-alkyl amines with good to excellent yields under mild and environmentally friendly conditions.

Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions

Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three

Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines

Triglycerides are used for the direct N-alkylation of amines with molecular hydrogen for the first time. A broad range of interesting and industrially relevant secondary and tertiary amines are obtained in the presence of an in situ formed Ru/Triphos complex. Notably, plant oil can be efficiently applied in this single-step process. Moreover, a variety of other methyl esters can be used as N-alkylation agents in the presence of hydrogen for the synthesis of more advanced building blocks.

[(NHC)Fe(CO)4]Efficient pre-catalyst for selective hydroboration of alkenes

[(IMes)Fe(CO)4] [IMes=1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene] complex was found to be an efficient pre-catalyst for the hydroboration of functional alkenes in the presence of pinacolborane at room temperature. Notably, UV irradiation

One-pot reductive n-alkylation with carbonyl compounds to give tertiary amines via borane reduction of imines

One-pot synthesis of tertiary amines via borane-mediated reduction of imines and reductive N-alkylation with carbonyl compounds is described. This protocols reducing agent is only borane in the reduction of imines, and additional reductant is not necessary in reductive N-alkylation step. When using more than two equivalents of aldehydes, reductive N-alkylation proceeded in good yield.

Amide activation by Tf2O: Reduction of amides to amines by NaBH4 under mild conditions

An expeditious and practical method for the reduction of amides to amines is reported. The method is consisted of activation of amides with Tf 2O followed by reduction with sodium borohydride in THF at room temperature. Various amides/lactams gave the corresponding amines in good to excellent yields, even with hindered amides and secondary amides. This method also presents other advantages such as TBDPS-group tolerance, short reaction time, simple workup and purification procedure. Georg Thieme Verlag Stuttgart.

Aminomethylation of organic halides promoted by zinc in protic medium

Organic halides undergo smooth aminomethylation by secondary amines and aqueous formaldehyde promoted by metallic zinc under copper(I) catalysis. Good to excellent yields are obtained with primary, secondary, and tertiary iodides, allylic, propargylic, and benzylic bromides and with α-bromoesters. In most cases, DMSO is the best solvent, but dioxane is preferable for some more reactive halides. Additional experiments with radical quenchers and promoters and the use of 'radical clocks' indicate a stepwise reaction mechanism initiated by the attack of an alkyl radical to iminium ion.

The reaction of amines with benzyl halides under CO2 atmosphere

To find a useful, practical, and ecologically safer way to synthesize protected amines, the reactions of amines with benzyl halides under CO2 atmosphere were systematically examined. For primary amines, the CO2-inserted products were obtained in higher yields in the presence of DBU as a base, under a high pressure of CO2, and in a low-polarity solvent (toluene/hexane 1:1). Secondary amines gave only low yields of CO2-inserted products.