207349-84-6

Usage

Uses

Used in Organic Synthesis:
N-(tert-butyl)-N-(3-methoxybenzyl)amine is used as a reagent for the production of various pharmaceuticals and agrochemicals. Its ability to promote the formation of essential chemical bonds makes it a crucial component in the synthesis of a wide range of organic compounds.
Used as a Catalyst in Chemical Reactions:
In the synthesis of organic compounds, N-(tert-butyl)-N-(3-methoxybenzyl)amine also serves as a catalyst, enhancing the efficiency and selectivity of reactions, which is particularly important in the production of complex organic molecules.
Used in Medicinal Chemistry for Drug Development:
N-(tert-butyl)-N-(3-methoxybenzyl)amine is utilized in medicinal chemistry for the development of new drugs. Its unique structural features and reactivity contribute to the design and synthesis of novel pharmaceutical agents, potentially leading to breakthroughs in the treatment of various diseases and conditions.

InChI:InChI=1/C12H19NO/c1-12(2,3)13-9-10-6-5-7-11(8-10)14-4/h5-8,13H,9H2,1-4H3

Upstream product

• 75-64-9 tert-butylamine 
• 591-31-1 3-methoxy-benzaldehyde 
• 824-98-6 m-methoxybenzyl chloride 
• 82632-37-9 N-tert-butyl-1-(3-methoxyphenyl)methanimine 

Downstream Products

• 207349-85-7 N-tert-Butyl-N-(3-methoxy-benzyl)-2-(2-p-tolylsulfanyl-phenyl)-acetamide 
• 1426960-18-0 N-(tert-butyl)-N-(3-methoxybenzyl)methacrylamide 
• 1628434-18-3 N-(tert-butyl)-2-chloro-N-(3-methoxybenzyl)acetamide 
• 1628434-34-3 (S)-1-(tert-butyl)-4-(3-methoxyphenyl)azetidin-2-one 
• 207349-88-0 N-tert-Butyl-N-(3-methoxy-benzyl)-2-[2-(toluene-4-sulfinyl)-phenyl]-acetamide 

Relevant academic research and scientific papers

Structure-Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines

The autoinduced, frustrated Lewis pair (FLP)-catalyzed hydrogenation of 16-benzene-ring substituted N-benzylidene-tert-butylamines with B(2,6-F2C6H3)3 and molecular hydrogen was investigated by kinetic analysis. The pKa values for imines and for the corresponding amines were determined by quantum-mechanical methods and provided a direct proportional relationship. The correlation of the two rate constants k1 (simple catalytic cycle) and k2 (autoinduced catalytic cycle) with pKa difference between imine and amine pairs (ΔpKa) or Hammett's σ parameter served as useful parameters to establish a structure-reactivity relationship for the FLP-catalyzed hydrogenation of imines.

Zirconium-Catalyzed Imine Hydrogenation via a Frustrated Lewis Pair Mechanism

Zirconium-based frustrated Lewis pairs (FLPs) are active imine hydrogenation catalysts under mild conditions. Complexes of the type [CpR2ZrOMes][B(C6F5)4] utilize the imine substrate itself as the Lewis base component of the FLP. Catalyst performance is a function of ligand structure; in general more bulky, more electron rich cyclopentadienyl derivatives give the best results. However, Cp? derivatives are not catalytically active, being stable after initial heterolytic cleavage of H2; this allows experimental verification of the competence of the zirconocene-imine pair in FLP-type heterolytic H2 cleavage. Enamines and protected nitriles are also hydrogenated if an additional internal phosphine base is used.

Reductive Transformations of Carbonyl Compounds Catalyzed by Rhodium Supported on a Carbon Matrix by using Carbon Monoxide as a Deoxygenative Agent

An efficient method for the rhodium on carbon matrix catalyzed preparation of secondary and tertiary amines, cyanoesters, and nitriles through the reductive amination/alkylation of carbonyl compounds was developed, including a convenient procedure for the tandem formal reductive addition of acetonitrile to aldehydes. The catalyst could be reused, and at least three consecutive reaction cycles were performed with comparable efficiency. The method was shown to be compatible with functional groups prone to reduction by hydrogen and complex hydrides. Beyond the matrix: An efficient method for the rhodium on carbon matrix catalyzed preparation of secondary and tertiary amines, cyanoesters, and nitriles through the reductive amination/alkylation of carbonyl compounds is developed, including a convenient procedure for the tandem formal reductive addition of acetonitrile to aldehydes. TON=turnover number.

Imine hydrogenation by alkylaluminum catalysts

Di-isobutylaluminum hydride and tri-iso-butylaluminum (DIBAL 1, TIBAL 2) are shown to be efficient hydrogenation catalysts for a variety of imines at 100 °C and 100 atm of H2, operating via a hydroalumination/ hydrogenolysis mechanism.

Kinetic study of the 7- endo selective radical cyclization of N-tert-butyl-o-bromobenzylmethacryl amides: Kinetic investigation of the cyclization and 1,7-hydrogen transfer of aromatic radicals

A kinetic investigation of the radical cyclization of N-tert-butyl-o- bromobenzylmethacryl amides to give 2-benzazepines via 7-endo selective cyclization was undertaken. The aryl radical generated from the amide precursor by treatment with Bu3SnH gave the three compounds, which are a 7-endo cyclized adduct, a 6-exocyclized adduct, and a reduced product. The cyclization reactions under various Bu3SnH concentrations were traced by GC analysis. The 7-endo/6-exo selectivity was constant irrespective of variation in Bu3SnH concentration. These results revealed that regioselectivity is controlled in a kinetic manner and that there is no possibility of a neophyl rearrangement. The use of Bu3SnD revealed that 1,7-hydrogen transfer, in which an aryl radical abstracts a hydrogen atom from the methallylic methyl group, occurs during the reaction. Hydrogen abstraction from toluene, the reaction solvent, was also observed. The 1,7-transfer rate depended on the Bu3SnX (X = H or D), and the reaction kinetics was examined. The kH/kD value for the hydrogen abstraction of aryl radical from Bu3SnX (X = H or D) was estimated using 4-bromoanisol. The utilization of these values revealed the overall reaction kinetics and relative rates for the cyclization and reduction by Bu3SnX (X = H or D). Kinetic parameters for hydrogen abstraction from toluene by aryl radicals were also estimated.

BORENIUM FRUSTRATED LEWIS PAIR CATALYSTS

A process for the catalytic hydrogenation of a variety of organic substrates using frustrated Lewis pair catalysts comprising a borenium complex is described. The frustrated Lewis pair catalysts described can also be used in a variety of chemical transformations of organic molecules.

Activation of hydrogen and hydrogenation catalysis by a borenium cation

The readily prepared borenium salt [(IiPr2)(BC8H 14)][B(C6F5)4] (2) [IiPr2 = C3H2(NiPr)2] is shown to activate H 2 heterolytically in the presence of tBu3P. Compound 2 also acts as a catalyst for the metal-free hydrogenation of imines and enamines at room temperature.

Additive and Vinylogous Pummerer Reactions of Amido Sulfoxides and Their Use in the Preparation of Nitrogen Containing Heterocycles

The α-thiocarbocation generated from the Pummerer reaction of N-methyl-N-phenyl-2-[2-(toluene-4-sulfinyl)phenyl]acetamide undergoes Friedel-Crafts reaction at the γ-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the related N-benzyl-N-alkyl amido sulfoxide system with trifluoroacetic anhydride affords tetrahydroisoquinolone derivatives. The product distribution encountered coincides with the rotamer population of the starting amide. When the N-benzyl-N-methyl amide is used, only the normal Pummerer product is formed. In this case, the thionium ion is generated in the wrong conformation for π-cyclization to occur. The corresponding N-tert-butyl amido system, however, exists in a geometric orientation which places the benzylic group in the crucial conformation necessary for π-cyclization, and consequently, the reaction proceeds smoothly. Related cyclization reactions occur in good yield with the corresponding furanyl and cyclohexenyl N-tert-butyl amido sulfoxides. The additive Pummerer reaction of 3-phenylsulfinyl-N-benzyl-N-tert-butylacrylamide gave products derived from both 5- and 6-exo trig cyclizations. Intramolecular electrophilic aromatic substitution via six-membered ring closure ultimately afforded a dihydropyridone. The competitive process involving ipso attack of the aromatic ring on the thionium ion generates a spiro cyclohexadienyl cation that undergoes fragmentation of the adjacent σ-bond. The resulting acyl iminium ion is converted to N-tert-butyl-2-phenyl-3-phenylsulfinylacrylamide upon aqueous workup. Only cyclizations leading to five-membered rings occur with the corresponding indolyl and alkenyl N-tert-butyl amido sulfoxides.