Retigabine Dihydrochloride

Base Information

• Chemical Name: Retigabine Dihydrochloride
• CAS No.: 150812-13-8
• Molecular Formula: C₁₆H₁₈FN₃O₂*ClH
• Molecular Weight: 339.797
• UNII: WV9W9019AP
• DSSTox Substance ID: DTXSID00164616
• Wikidata: Q27292919
• Mol file: 150812-13-8.mol

Synonyms:Retigabine Dihydrochloride;150812-13-8;Ezogabine Dihydrochloride;Retigabine (dihydrochloride);Retigabine 2HCl;UNII-WV9W9019AP;WV9W9019AP;ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate;dihydrochloride;Retigabine hydrochloride;D20443 dihydrochloride;D 23129 hydrochloride;SCHEMBL155918;DTXSID00164616;Retigabine dihydrochloride- Bio-X;D-23129 2HCl;BCP07747;HY-15471A;s4734;EZOGABINE DIHYDROCHLORIDE [MI];AKOS015994594;AC-5274;ADD-172014;CCG-268364;CS-1136;HE-0244;BR164335;LS-191294;D23129;E98674;Q27292919;N-(2-amino-4-[fluorobenzylamino]-phenyl) carbamic acid (2HCl);ethyl 2-amino-4-(4-fluorobenzylamino)phenylcarbamate dihydrochloride;ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate dihydrochloride;CARBAMIC ACID, N-(2-AMINO-4-(((4-FLUOROPHENYL)METHYL)AMINO)PHENYL)-, ETHYL ESTER, HYDROCHLORIDE (1:2);N-(2-AMINO-4-(((4-FLUOROPHENYL)METHYL)AMINO)PHENYL)CARBAMIC ACID ETHYL ESTER DIHYDROCHLORIDE

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Chemical Property of Retigabine Dihydrochloride

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Melting Point: 168-170°C
• Boiling Point: 430 °C at 760 mmHg
• Flash Point: 213.9 °C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: ≥18.8 mg/mL in DMSO; ≥52.4 mg/mL in H2O with gentle warming; ≥8.71 mg/mL in EtOH with gentle warming and ultrasonic
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 375.0916604
• Heavy Atom Count: 24
• Complexity: 348

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N.Cl.Cl

Technology Process of Retigabine Dihydrochloride

There total 10 articles about Retigabine Dihydrochloride 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: 91.6%

Retigabine (150812-12-7) → retigabine dihydrochloride (150812-13-8)

Guidance literature:

With hydrogenchloride; In methanol; at 25 - 30 ℃; for 2h; Solvent; Time;

Reference yield: 62.5%

Retigabine (150812-12-7) → ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate hydrochloride (1215347-18-4,150812-13-8)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 2h;

Reference yield:

4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine (491871-67-1) + chloroformic acid ethyl ester (541-41-3) → retigabine dihydrochloride (150812-13-8)

Guidance literature:

4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine; chloroformic acid ethyl ester; With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 10 - 20 ℃;

With hydrogenchloride; In 1,4-dioxane; water; isopropyl alcohol; at 0 - 20 ℃;

upstream raw materials:

4-N-[(4-fluorophenyl)methyl]benzene-1,2,4-triamine

chloroformic acid ethyl ester

2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene

4-fluorobenzaldehyde

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF RETIGABINE OF THE FORMULA I AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF". . . Retrieved 2013/03/26.