Levlofexidine

Base Information

• Chemical Name: Levlofexidine
• CAS No.: 81447-78-1
• Molecular Formula: C11H12Cl2N2O
• Molecular Weight: 259.135
• UNII: 5SPW497X0Z
• DSSTox Substance ID: DTXSID201024657
• Nikkaji Number: J33.078G
• Wikidata: Q27262818
• NCI Thesaurus Code: C81366
• ChEMBL ID: CHEMBL2107417
• Mol file: 81447-78-1.mol

Synonyms:Levlofexidine;81447-78-1;(R)-Lofexidine;Levlofexidine [INN];Lofexidine, (r)-;2-[(1R)-1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole;UNII-5SPW497X0Z;5SPW497X0Z;(-)-(R)-2-(1-(2,6-Dichlorophenoxy)ethyl)-2-imidazoline;(R)-2-(1-(2,6-Dichlorophenoxy)ethyl)-4,5-dihydro-1H-imidazole;SCHEMBL947241;CHEMBL2107417;BDBM85233;DTXSID201024657;CAS_81447-78-1;(R)-2-(1-(2,6-Dichlorophenoxy)ethyl)-2-imidazoline;Q27262818;(-)-(R)-2-(1-(2,6-Dichlorophenoxy)ethyl)-2-imidazoline.

Chemical Property of Levlofexidine

Chemical Property:

• Vapor Pressure: 6.35E-07mmHg at 25°C
• Boiling Point: 421.5°Cat760mmHg
• Flash Point: 208.7°C
• PSA: 33.62000
• Density: 1.39g/cm³
• LogP: 2.52680
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 258.0326684
• Heavy Atom Count: 16
• Complexity: 263

Purity/Quality:

98% ^*data from raw suppliers

(R)-Lofexidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=NCCN1)OC2=C(C=CC=C2Cl)Cl
• Isomeric SMILES: C[C@H](C1=NCCN1)OC2=C(C=CC=C2Cl)Cl
• Uses: Levlofexidine is the R-enantiomer of Lofexidine,it is a α2-Adrenoceptor agonist related structurally to Clonidine, Used in treatment of opioid withdrawal symptoms; antihypertensive.

Technology Process of Levlofexidine

There total 16 articles about Levlofexidine 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: 99.0%

lofexidine (73372-53-9,81447-78-1,81447-79-2,31036-80-3) → (-)-Lofexidine (81447-78-1)

Guidance literature:

In acetone; for 24h; Ambient temperature;

DOI:10.1021/jm00157a011

Reference yield: 90.0%

(±)ethyl 2-(2,6-dichlorophenoxy)propionate (344559-34-8,86981-78-4) + ethylenediamine (107-15-3,85404-18-8) → lofexidine (73372-53-9,81447-78-1,81447-79-2,31036-80-3)

Guidance literature:

ethylenediamine; With titanium(IV) isopropylate; In toluene; at 20 ℃; for 1h; Inert atmosphere;

(±)ethyl 2-(2,6-dichlorophenoxy)propionate; In toluene; at 110 ℃; for 18h; Time; Inert atmosphere;

Reference yield: 85.0%

ethylenediamine (107-15-3,85404-18-8) + (R)-(-)-2-(2,6-dichlorophenoxy)propionamide (87789-42-2) → (-)-Lofexidine (81447-78-1)

Guidance literature:

(R)-(-)-2-(2,6-dichlorophenoxy)propionamide; With trimethoxonium tetrafluoroborate; In dichloromethane; for 36h;

ethylenediamine; In dichloromethane; at 0 - 20 ℃;

upstream raw materials:

2-(2,6-dichlorophenoxy)-propionitrile

ethylenediamine

2,6-Dichlorophenol

C₁₀H₁₀Cl₂O₃

Downstream raw materials:

(+)-Lofexidine

(-)-Lofexidine hydrochloride

lofexidine hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF LOFEXIDINE". . . Retrieved 2021/10/22.
• 2、 -. "LOFEXIDINE ENANTIOMERS FOR USE AS A TREATMENT FOR CNS DISEASE AND PATHOLOGIES AND ITS CHIRAL SYNTHESIS". Page/Page column 10. . Retrieved 2010/04/03.