1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol

Base Information

• Chemical Name: 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol
• CAS No.: 5653-66-7
• Molecular Formula: C11H17 N O3
• Molecular Weight: 211.261
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80961983
• Nikkaji Number: J2.377.342B
• Mol file: 5653-66-7.mol

Synonyms:N-methyl-3,4-dimethoxy-beta-hydroxy-beta-phenethylamine;normacromerine;normacromerine hydrochloride;normacromerine hydrochloride, (+-)-isomer;normacromerine, (+-)-isomer;normacromerine, (R)-isomer

Chemical Property of 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol

Chemical Property:

• Vapor Pressure: 1.19E-05mmHg at 25°C
• Boiling Point: 284.7°Cat760mmHg
• Flash Point: 126°C
• PSA: 50.72000
• Density: g/cm³
• LogP: 1.34750
• Sensitive.: Air Sensitive
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 211.12084340
• Heavy Atom Count: 15
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C1=CC(=C(C=C1)OC)OC)O
• Description: This phenethylamine type alkaloid has recently been discovered in Coryphantha macromeris. It is characterized as the crystalline hydrochloride, m.p. 132-3°C. The structure, as determined from chemical and spectroscopic analysis is {j_x0002_hydroxy-3:4-dimethoxy-N-methyl-{j-phenethylamine.

Technology Process of 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol

There total 16 articles about 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.1%

1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride (40511-15-7) → N-methylhomoveratrylamine (3490-06-0) + 1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol (5653-66-7)

Guidance literature:

1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride; With hydrogen; 5%-palladium/activated carbon; In water; at 75 ℃; for 16 - 40h; under 2585.81 Torr;

With sodium hydroxide; In water; toluene; pH=12; Product distribution / selectivity;

Reference yield: 52.0%

3’-methyl-10H-spiro[anthracene-9,5’-oxazolidin]-10-one + 3,4-dimethoxy-benzaldehyde (120-14-9) → 1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol (5653-66-7)

Guidance literature:

In o-xylene; at 210 ℃; for 1.33h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acs.orglett.6b00475

Reference yield:

C12H17NO3 → 1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol (5653-66-7)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 45h; Reflux;

DOI:10.1016/j.tetlet.2013.08.083

upstream raw materials:

3,4-dimethoxy-DL-mandelic acid-methylamide

N-methyl-N-benzyl-2-(3,4-dimethoxyphenyl)-2-hydroxyethylamine

1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride

ethanol

Downstream raw materials:

(+/-)-2-(acetyl-methyl-amino)-1-(3,4-dimethoxy-phenyl)-ethanol

methylamine

Refernces

Facile synthesis of glycol metabolites of phenethylamine drugs

10.1002/jps.2600750621

The research describes a facile synthesis method for glycol metabolites of phenethylamine drugs, including potential metabolites of psynephrine, epinephrine, octopamine, and normacromerine. The purpose of this study was to develop a general synthetic scheme that yields high quantities of these metabolites using readily available monosubstituted and disubstituted acetophenones, overcoming challenges such as dimerization and pinacol-pinacolone rearrangement inherent in aromatic glycol synthesis. The process involved alpha-bromination, displacement with acetate ion, and reduction with lithium aluminum hydride, resulting in yields ranging from 46 to 91%.