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Usage

Uses

Used in Pharmaceutical Industry:
N-(Diphenylmethyl)methylamine is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its steric hindrance and reactivity contribute to the formation of complex molecular structures that are essential in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-(Diphenylmethyl)methylamine is used as a reagent in the preparation of cyclooctene oxide, a key intermediate in the synthesis of various organic compounds. Its unique properties allow for selective reactions and the formation of specific products with desired characteristics.
Used in Research and Development:
N-(Diphenylmethyl)methylamine is also utilized in research and development laboratories for the study of organic reactions and the development of new synthetic methods. Its steric hindrance and reactivity make it an interesting subject for exploring new reaction pathways and understanding the underlying mechanisms.

InChI:InChI=1/C14H15N/c1-15-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11,14-15H,1H3

Upstream product

• 119-61-9 benzophenone 
• 96-31-1 N,N'-Dimethylurea 
• 74-89-5 methylamine 
• 13280-16-5 N-(diphenylmethylene)methylamine 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 622-29-7 N-Benzylidenemethylamine 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 100-58-3 phenylmagnesium bromide 
• 91-00-9 Benzhydrylamine 
• 67-56-1 methanol 
• 1013-88-3 Benzophenone imine 
• 591-51-5 phenyllithium 
• 23728-68-9 N-Methyl-N-(trimethylsilyl)benzamide 
• 3376-23-6 C-phenyl-N-methylnitrone 

Downstream Products

• 171669-60-6 4-N-methyl-N-benzhydrylamino-5-methoxy-1,2-benzoquinone 
• 94192-78-6 N-diphenylmethyl-N-methyl-4-(2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutyramide 
• 1427204-05-4 4-{[(diphenylmethyl)(methyl)amino]methyl}-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate 

Relevant academic research and scientific papers

On the Virtue of Indium in Reduction Reactions. A Comparison of Reductions Mediated by Indium and Zinc: Is Indium Metal an Effective Catalyst for Zinc Induced Reductions?

Indium(0)-mediated reductions have been reported for the transformation of several functional groups (imines, oximes, nitro groups, isoxazolidines, and conjugated alkenes, among others), prompted by the opportunity of performing the reactions in aqueous media and green conditions. We describe here the comparison of several reactions using indium or the less expensive zinc, carried out in order to evaluate the effective advantages brought about indium metal. We found some reactions for which use of In is mandatory and others where Zn worked equally well or even better. The reduction of hydroxylamines to the corresponding amines was the only reduction for which use of In provided much better results than Zn and was also possible to apply an efficient catalytic version with use of 2–5 mol-% In in the presence of stoichiometric Zn. Applicability of this catalytic reduction to “one-pot” model processes is also demonstrated.

Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.

The reductive cleavage of picolinic amides

Treatment of picolinic amides with excess zinc in aqueous hydrochloric acid at room temperature affords the corresponding amines in good to excellent yields. The mild reaction conditions exhibit useful functional group tolerance and facilitate the application of the picolinic amide moiety as a protecting group which can be easily introduced and selectively removed.

Methyl fluoroalkanoate as methyl-transferring reagent. Unexpected participation of BAl2 (SN2) mechanism in the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with amines

In the reaction of methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate with arylamines or arylmethylamines, an unexpected methyl transfer from the ester to the amine by the BAl2 (SN2) mechanism was observed leading to the corresponding N-methylamines under specific conditions. The reaction was accompanied by the formation of amides via BAc2 mechanism. The unexpected methyl transfer is highly dependent on the structure of the starting amine and is supported by the absence of solvent and high temperature.

Methanol dehydrogenation by iridium N-heterocyclic carbene complexes

A series of homogeneous iridium bis(N-heterocyclic carbene) catalysts are active for three transformations involving dehydrogenative methanol activation: acceptorless dehydrogenation, transfer hydrogenation, and amine monoalkylation. The acceptorless dehydrogenation reaction requires base, yielding formate and carbonate, as well as 2-3 equivalents of H2. Of the few homogeneous systems known for this reaction, our catalysts tolerate air and employ simple ligands. Transfer hydrogenation of ketones and imines from methanol is also possible. Finally, N-monomethylation of anilines occurs through a borrowing hydrogen reaction. Notably, this reaction is highly selective for the monomethylated product.

Enhanced reduction of C-N multiple bonds using sodium borohydride and an amorphous nickel catalyst

Amorphous nickel powder (Ni0) was utilised as a catalyst under mild, aqueous, basic conditions for enhancing the sodium borohydride-mediated reduction of C-N multiple bonds such as oximes, imines, hydrazones and nitriles to produce the corresponding amines in good to excellent yields.

Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright

ASYMMETRIC IMINE HYDROGENATION PROCESSES

A process for the catalytic hydrogenation or asymmetric hydrogenation of imines of Formula (I) to the corresponding amines of Formula (II) is provided in which R1 is aryl ; R2 is aryl, cyclic, alkyl, alkenyl or alkynyl; and R3 is alky l. The catalytic system includes a ruthenium complex containing (1) a diamine and (2) a diphosphine or two monodentate phosphines ligands. Such process also relates to the asymmetric hydrogenation of prochiral imines to the chiral amines using chiral ruthenium complexes bearing chiral diphosphines or chiral monodentate phosphines and chiral diamines.

Indium-mediated reduction of hydroxylamines to amines

(Matrix presented) A novel and simple procedure for reduction of hydroxylamines to the corresponding amines by means of indium powder in aqueous media is reported. Applicability to one-pot reactions and isoxazolidine N-O bond reduction is also demonstrated. A catalytic version of the process using 2-5% In in the presence of other metals (Zn, Al) has been successfully developed.

Synthesis of N-methyl secondary amines

A diverse set of N-methyl secondary amines are obtained in high yields by an expedient reductive alkylation of commercially available methanolic methylamine.