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

Base Information

• Chemical Name: 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanol
• CAS No.: 41787-64-8
• Molecular Formula: C11H17NO3
• Molecular Weight: 211.261
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID80961983
• Nikkaji Number: J2.377.342B
• Mol file: 41787-64-8.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:

• Boiling Point: 354.9°Cat760mmHg
• Flash Point: 168.5°C
• PSA: 50.72000
• Density: 1.089g/cm³
• LogP: 1.34750
• Storage Temp.: 4°C, Inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Sparingly). Ethyl Acetate, Methanol
• 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

(-)-Normacromerine ^*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
• Uses: A metabolite of of phenethylamine drugs, normally isolated from Dona Ana cactus, having similar psychoactive properties as Mescaline or Psilocin (P839630). A metabolite of phenethylamine drugs, normally isolated from Dona Ana cactus, having similar psychoactive properties as Mescaline or Psilocin (P839630).

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

There total 8 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: 91.0%

(4R,5R)-5-(3,4-Dimethoxy-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole (131065-69-5) → (R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol (41787-64-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00311a007

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol (41787-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: silver triflate-chiral ligand 1a / CH₂Cl₂ / 2 h / 25 °C

2: 91 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

With lithium aluminium tetrahydride; silver triflate-chiral ligand 1a; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00311a007

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (R)-1-(3,4-Dimethoxy-phenyl)-2-methylamino-ethanol (41787-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (-)-2-(2-HO-3-Br-5-t-Bu-C₆H₂-CH=N)-2'-HO-1,1'-binaphthyl, Ti(O-iPr)4, 2-HO-3,5-t-Bu₂-C₆H₂-COOH, 2.) Me₃SiCl, Et₃N, 4.) TFA / 1.) toluene, 23 deg C, 1 h and 1 h, 23 deg C, 2.) toluene, -20 deg C, 15 min, 3.) toluene, -20 deg C to 23 deg C, 6 h, 4.) THF

2: imidazole / dimethylformamide

3: NaOH / H₂O; methanol

4: SOCl₂

5: NH₄OH

6: 1.) PhI(OAc)2, KOH, 2.) LiAlH₄ / 2.) THF, heating

With 1H-imidazole; titanium(IV) isopropylate; potassium hydroxide; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; thionyl chloride; [bis(acetoxy)iodo]benzene; (-)-2-(2-HO-3-Br-5-t-Bu-C₆H₂-CH=N)-2'-HO-1,1'-binaphthyl; 3,5-ditertbutyl salicylic acid; triethylamine; trifluoroacetic acid; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)02515-4

upstream raw materials:

(4R,5R)-5-(3,4-Dimethoxy-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole

3,4-dimethoxy-benzaldehyde

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(3,4-dimethoxy-phenyl)-propionic acid

(S)-3-(3,4-Dimethoxy-phenyl)-3-hydroxy-propionic acid benzyl ester

Downstream raw materials:

L-epinephrine