53663-28-8

Usage

Uses

Used in Pharmaceutical Industry:
(2,3-DIMETHOXYBENZYL)METHYLAMINE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can exhibit therapeutic properties.
Used in Organic Chemistry Research:
(2,3-DIMETHOXYBENZYL)METHYLAMINE is used as a reagent in organic chemistry research, facilitating the development of new synthetic pathways and the study of chemical reactions involving amines and benzyl groups.
Used in Natural Products Synthesis:
(2,3-DIMETHOXYBENZYL)METHYLAMINE is used as a key component in the synthesis of natural products, enabling the replication of complex natural compounds with potential biological activities.
It is important to handle (2,3-DIMETHOXYBENZYL)METHYLAMINE with care, as it is a potentially hazardous substance. It should only be used by trained professionals in a controlled laboratory environment to ensure safety and proper utilization in its respective applications.

InChI:InChI=1/C10H15NO2/c1-11-7-8-5-4-6-9(12-2)10(8)13-3/h4-6,11H,7H2,1-3H3/p+1

Upstream product

• 3893-01-4 2,3-dimethoxybenzyl chloride 
• 74-89-5 methylamine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 722495-95-6 (2,3-dimethoxy-benzylidene)-methyl-amine 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 128942-62-1 2-[(2,3-dimethoxy-benzyl)-methyl-amino]-1-phenyl-ethanol 
• 100252-63-9 2-[(2,3-dimethoxy-benzyl)-methyl-amino]-ethanol 
• 128942-56-3 2-[(2,3-Dimethoxy-benzyl)-methyl-amino]-1-phenyl-ethanone 
• 128942-66-5 7,8-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 131254-48-3 [2-(3-amino-propoxy)-ethyl]-(2,3-dimethoxy-benzyl)-methyl-amine 
• 102873-52-9 3-{2-[(2,3-dimethoxy-benzyl)-methyl-amino]-ethoxy}-propionitrile 
• 1208333-38-3 C₁₃H₂₁NO₃ 
• 1262999-65-4 2-((2,3-dimethoxybenzyl)(methyl)amino)benzaldehyde 

Relevant academic research and scientific papers

Highly enantioselective synthesis of tetrahydroquinolines via cobalt(II)-catalyzed tandem 1,5-hydride transfer/cyclization

A chiral catalyst prepared from N,N′-dioxide and Co(BF 4)2·6H2O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.

A novel construction of 2-benzazepine scaffold based on TiCl 4-mediated tandem Mannich reaction - Aromatic electrophilic substitution

A novel construction of 2-benzazepine derivatives based on TiCl 4-mediated tandem Mannich reaction of electron-rich benzyl iminium ions with alkenyl ethers and Friedel - Crafts-type alkylation is described. The protocol is amenable to provide the tricyclic furo[3,2-d][2]benzazepine and pyrano[3,2-d][2]benzazepine derivatives, respectively, with 2,3-dihydrofuran or 3,4-dihydro-2H-pyran as the substrates.

Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbamic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases.

A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines

1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines 6 are obtained from aromatic aldehydes 1, methyl amine and α-haloacetophenones 2 in the presence of sodium borohydride followed by cyclization with sulfuric acid and zinc in methanol.