60951-19-1

Usage

Uses

Used in Pharmaceutical Industry:
Benzeneethanamine, N-ethyl-a-phenylis used as an intermediate in the synthesis of various pharmaceuticals and drugs. Its unique structure and properties contribute to the development of medications with potential therapeutic applications.
Used in Research and Development:
Benzeneethanamine, N-ethyl-a-phenylis utilized in research settings to study the relationship between chemical structure and biological activity. Its psychoactive properties and potential as a central nervous system stimulant make it a valuable subject for exploring the mechanisms of action and potential applications in medicinal chemistry.

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 75-04-7 ethylamine 
• 6852-54-6 N-(benzylidene)ethylamine 
• 501-65-5 diphenyl acetylene 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 64857-61-0 diethyl-bibenzyl-α-yl-amine 

Relevant academic research and scientific papers

Tertiary amine synthesis: Via reductive coupling of amides with Grignard reagents

A new iridium catalyzed reductive coupling reaction of Grignard reagents and tertiary amides affording functionalised tertiary amine products via an efficient and technically-simple one-pot, two-stage experimental protocol, is reported. The reaction-which can be carried out on gram-scale using as little as 1 mol% Vaska's complex [IrCl(CO)(PPh3)2] and TMDS as the terminal reductant for the initial reductive activation step-tolerates a broad range of tertiary amides from (hetero)aromatic to aliphatic (branched, unbranched and formyl) and a wide variety of alkyl (linear, branched), vinyl, alkynyl and (hetero)aryl Grignard reagents. The new methodology has been applied directly to bioactive molecule synthesis and the high chemoselectivity of the reductive coupling of amide has been exploited in late stage functionalization of drug molecules. This reductive functionalisation of tertiary amides provides a new and practical solution to tertiary amine synthesis.

Ind2TiMe2-catalyzed addition of methyl- and ethylamine to alkynes

We describe a very simple hydrogenation-like experimental protocol for the addition of gaseous methyl- and ethylamine to alkynes in the presence of Ind2TiMe2 as the catalyst. For efficient hydroamination reactions it is sufficient to stir a mixture of the alkyne and the catalyst in toluene at temperatures between 80°C (terminal alkynes) and 105°C (internal alkynes) under a constant pressure of 1 atm of the corresponding amine. After subsequent reduction of the initially formed imines, methyl- and ethylamine derivatives are the final products of the described one-pot reaction sequences. In the case of 2-alkyl-1-phenylalkynes as starting materials, biologically interesting 2-phenylethylamine derivatives possessing a small methyl or ethyl substituent at the N atom are easily accessible by the new reaction protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

WCl6/LiAlH4 PROMOTED TRANSFORMATION OF IMINES INTO SECONDARY AND TERTIARY AMINES

The reaction of WCl6/LiAlH4 with imines, R'N=CHR, gave tertiary amines, R'N(CH2R)2, and secondary amines, R'NHCHRCH2R.Isotope labeling experiments revealed that the reaction involved two types of azatungstenacyclobutanes, , produced from the reaction of an alkylidene tungsten intermediate with the imine C=N double bond.Formation of these metallacyclobutanes is highly dependent on the solvent used.