104338-26-3

Basic information

• Product Name: [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE
• Synonyms: [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE;2-METHOXY-N-METHYL-BENZENEETHANAMINE;OTAVA-BB 7020694233;N-[2-(2-Methoxyphenyl)ethyl]-N-methylamine;2-(2-Methoxyphenyl)-N-methylethanamine
• CAS NO: 104338-26-3
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.234
• Mol File: 104338-26-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE(104338-26-3)
• EPA Substance Registry System: [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE(104338-26-3)

Safety Data

• Hazardous Substances Data: 104338-26-3(Hazardous Substances Data)

Usage

General Description

[2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE is a chemical compound that is composed of a 2-(2-methoxyphenyl)ethyl group bound to a methylamine group. It is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds. [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE is known for its role in the production of various drugs, such as antihistamines and antidepressants. It is also used in chemical reactions as a reagent or building block for the synthesis of other organic compounds. Additionally, it is important to handle this chemical with caution as it can be hazardous if not used properly.

Upstream product

• 2045-79-6 o-methoxy-2-phenylethylamine 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 6342-77-4 2-methoxy-benzenepropanoic acid 
• 59734-18-8 3-(2-methoxy-phenyl)-propionic acid amide 
• 131699-15-5 N-(t-Butyloxycarbonyl)-2-(2-methoxyphenyl)-ethylamine 
• 258882-54-1 N-(methoxycarbonyl)-2-(2-methoxyphenyl)ethylamine 

Downstream Products

• 69226-64-8 N-(2-methoxy-phenethyl)-N-methyl-urea 
• 154585-18-9 2-(2-methylamino-ethyl)-phenol 
• 1282042-14-1 C₂₀H₂₂N₄O₂ 

Relevant articles and documents

Palladium-Catalyzed C(sp2)-H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

A rapid construction of THIQs by a Pd(II)-catalyzed C(sp2)-H olefination of free primary and secondary 2-phenylethylamines with high step- and atom-economy was reported. Notably, no substituent was required at the α-position to the amino group of the 2-phenylethylamines. The substrate scope was broad, and the reaction could also be applied to generate THIQs from the biologically active molecules such as the drug molecule baclofen and phenylalanine ester.

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

Selective N-methylation of primary aliphatic amines with dimethyl carbonate in the presence of alkali cation exchanged Y-faujasites

The N-methylation of aliphatic amines [XC6H4(CH 2)nNH2; n=1, X=H (1a), o-MeO (1b), p-MeO (1c); n=2, X=H (2a), o-MeO (2b); 1d: PhCH(Me)NH2] with dimethyl carbonate (DMC) is efficiently catalysed by NaY faujasite: on condition that CO 2 (a co-product of the reaction) is carefully removed, N-methyl- and N,N-dimethyl-amines (RNHMe and RNMe2) are obtained in good overall yields (70-90%). Otherwise, in the presence of CO2, carbamates (RNHCO2Me) form competitively to a large extent. The reaction probably proceeds through a BAl2 displacement of the amine on DMC.