N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide

Base Information

• Chemical Name: N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide
• CAS No.: 344443-16-9
• Molecular Formula: C11H14Cl2N2O2
• Molecular Weight: 277.15
• European Community (EC) Number: 695-822-5
• UNII: YT24TXU38S
• DSSTox Substance ID: DTXSID10524944
• Mol file: 344443-16-9.mol

Synonyms:N-(2-AMINOETHYL)-2-(2,6-DICHLOROPHENOXY)PROPANAMIDE;344443-16-9;YT24TXU38S;Lofexidine metabolite (ladp);UNII-YT24TXU38S;Propanamide, N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)-;IYGPXILYSHJRMS-UHFFFAOYSA-N;SCHEMBL10778352;DTXSID10524944;(+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide;(-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide;(+)-2-(2,6 -dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide

Chemical Property of N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide

Chemical Property:

• Boiling Point: 471.1 °C at 760 mmHg
• PKA: 14.12±0.46(Predicted)
• Flash Point: 238.7 °C
• PSA: 67.84000
• Density: 1.299 g/cm³
• LogP: 3.37620
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 276.0432331
• Heavy Atom Count: 17
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NCCN)OC1=C(C=CC=C1Cl)Cl
• Uses: Lofexidine intermediate.

Technology Process of N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide

There total 3 articles about N-(2-Aminoethyl)-2-(2,6-dichlorophenoxy)propanamide 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: 79.9%

(±)ethyl 2-(2,6-dichlorophenoxy)propionate (344559-34-8,86981-78-4) + ethylenediamine (107-15-3,85404-18-8) → (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide (344443-16-9)

Guidance literature:

at 20 ℃; for 2h; Inert atmosphere; Reflux;

Reference yield: 30.0%

C10H10Cl2O3 (1112401-07-6) + ethylenediamine (107-15-3,85404-18-8) → (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide (344443-16-9) + lofexidine (73372-53-9,81447-78-1,81447-79-2,31036-80-3)

Guidance literature:

at 0 ℃; for 8h; Time; Mechanism;

DOI:10.1021/op8002689

Reference yield:

2,6-Dichlorophenol (87-65-0) → (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide (344443-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / dimethyl sulfoxide / 4 h / 20 - 65 °C / Inert atmosphere

2: 2 h / 20 °C / Inert atmosphere; Reflux

With potassium carbonate; In dimethyl sulfoxide;

upstream raw materials:

C₁₀H₁₀Cl₂O₃

ethylenediamine

2,6-Dichlorophenol

(±)ethyl 2-(2,6-dichlorophenoxy)propionate

Refernces

• 1、 Vartak, Ashish P.,Crooks, Peter A.. "A scalable, enantioselective synthesis of the r2-adrenergic agonist, lofexidine". body text. p. 415 - 419. Retrieved 2010/04/22.