Flunarizine

Base Information

• Chemical Name: Flunarizine
• CAS No.: 52468-60-7
• Molecular Formula: C26H26F2N2
• Molecular Weight: 404.503
• European Community (EC) Number: 257-937-5,254-842-0
• UNII: R7PLA2DM0J
• DSSTox Substance ID: DTXSID6045616
• Nikkaji Number: J291.228G,J9.934A
• Wikipedia: Flunarizine
• Wikidata: Q416237
• NCI Thesaurus Code: C83718
• Pharos Ligand ID: FH1AY465SJH3
• Metabolomics Workbench ID: 43629
• ChEMBL ID: CHEMBL30008
• Mol file: 52468-60-7.mol

Synonyms:Dihydrochloride, Flunarizine;Flunarizin;Flunarizine;Flunarizine Dihydrochloride;Flunarizine Hydrochloride;Hydrochloride, Flunarizine;R 14950;R-14950;R14950;Sibelium

Chemical Property of Flunarizine

Chemical Property:

• Vapor Pressure: 1.43E-10mmHg at 25°C
• Refractive Index: 1.606
• Boiling Point: 511.3 °C at 760 mmHg
• PKA: 6.99±0.10(Predicted)
• Flash Point: 263 °C
• PSA: 6.48000
• Density: 1.17 g/cm³
• LogP: 5.26100
• Storage Temp.: 2-8°C
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 404.20640516
• Heavy Atom Count: 30
• Complexity: 487

Purity/Quality:

99% ^*data from raw suppliers

Flunarizine-d8dHCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
• Isomeric SMILES: C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
• Recent ClinicalTrials: Evaluation of Efficacy and Safety of add-on Alpha-lipoic Acid on Migraine Prophylaxis in Adolescent Population
• Uses: Vasodilator.
• Therapeutic Function: Vasodilator

Technology Process of Flunarizine

There total 15 articles about Flunarizine 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: 89.0%

1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-chloroprop-2-en-1-yl]piperazine + phenylmagnesium chloride (100-59-4) → flunarizine (52468-60-7)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate; In tetrahydrofuran; at 0 - 20 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1134/S107036321608034X

Reference yield: 87.0%

sodium (E)-1-hydroxy-3-phenylprop-2-ene-1-sulfonate (75145-31-2) + 1-(4-fluorophenyl)methyl-piperazine (27469-60-9) → flunarizine (52468-60-7)

Guidance literature:

With 2-picoline borane complex; In methanol; water; at 60 ℃; for 6h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02604

Reference yield: 86.0%

4-fluoro-1-iodobenzene (352-34-1) + 1-cinnamyl-4-(trimethylsilyl)piperazine + 4-fluorobenzaldehyde (459-57-4) → flunarizine (52468-60-7)

Guidance literature:

1-cinnamyl-4-(trimethylsilyl)piperazine; 4-fluorobenzaldehyde; With t-butyldimethylsiyl triflate; In 1,4-dioxane; for 0.05h; Inert atmosphere; Glovebox;

4-fluoro-1-iodobenzene; With nickel(II) bromide dimethoxyethane; 2,6-bis(pyrazole)pyridine; zinc; In 1,4-dioxane; at 50 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.7b12212

upstream raw materials:

1-(4-fluorophenyl)methyl-piperazine

(2E)-3-phenyl-2-propen-1-ol

1-(4,4’-difluorophenylmethyl)-4-(2-acetaldehyde)piperazine

benzyltriphenylphosphonium chloride

Refernces

• 1、 Bailey, J. Daniel,Iyer, Karthik S.,Leahy, David K.,Li, Xiaohan,Lipshutz, Bruce H.,Thakore, Ruchita R.. "Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water". supporting information. p. 7205 - 7208. Retrieved 2021/09/22.
• 2、 Sweeney, Joseph B.,Ball, Anthony K.,Lawrence, Philippa A.,Sinclair, Mackenzie C.,Smith, Luke J.. "A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols". supporting information. p. 10202 - 10206. Retrieved 2018/08/06.