Vanoxerine

Base Information

• Chemical Name: Vanoxerine
• CAS No.: 67469-69-6
• Molecular Formula: C28H32F2N2O
• Molecular Weight: 450.572
• UNII: 90X28IKH43
• DSSTox Substance ID: DTXSID8045143
• Nikkaji Number: J259.982A
• Wikipedia: Vanoxerine
• Wikidata: Q2510480
• NCI Thesaurus Code: C81084
• Pharos Ligand ID: X3Z4X23VJL4Y
• Metabolomics Workbench ID: 63138
• ChEMBL ID: CHEMBL281594
• Mol file: 67469-69-6.mol

Synonyms:1-(2 (bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine;1-(2 (bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride;GBR 12909;GBR-12909;I 893;I-893;vanoxeamine;vanoxerine

Chemical Property of Vanoxerine

Chemical Property:

• Vapor Pressure: 7.7E-12mmHg at 25°C
• Boiling Point: 542.7°Cat760mmHg
• PKA: 7.55±0.10(Predicted)
• Flash Point: 282°C
• PSA: 15.71000
• Density: 1.135g/cm³
• LogP: 5.19700
• Solubility.: Soluble in DMSO
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 450.24826997
• Heavy Atom Count: 33
• Complexity: 498

Purity/Quality:

99% ^*data from raw suppliers

Vanoxerine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
• Recent ClinicalTrials: Interaction Between Vanoxerine (GBR 12909) and Cocaine in Cocaine Dependent Individuals
• Recent EU Clinical Trials: RESTORE SR: A multi-center, Randomized, double-blind, placebo-controlled study to Evaluate the Safety and efficacy of a single oral dose of vanoxerine for The conversion Of subjects with REcent onset atrial fibrillation or flutter to normal Sinus Rhythm

Technology Process of Vanoxerine

There total 5 articles about Vanoxerine 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:

1-(3-phenylpropyl)-piperazine dihydrochloride + 2-[bis(4-fluorophenyl)methoxy]ethyl iodide (321365-84-8) → 1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazine (67469-69-6)

Guidance literature:

With sodium carbonate; In water; butanone; at 75 - 80 ℃; for 24h; Concentration; Reagent/catalyst; Time; Solvent; Large scale;

DOI:10.1021/op020211j

Reference yield:

1-Bromo-3-phenylpropane (637-59-2) → 1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazine (67469-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 8 h / 75 - 80 °C / Large scale

2: hydrogenchloride / ethanol / 2 h / 20 - 30 °C / Large scale

3: sodium carbonate / water; butanone / 24 h / 75 - 80 °C / Large scale

With hydrogenchloride; sodium carbonate; In ethanol; water; acetonitrile; butanone;

DOI:10.1021/op020211j

Reference yield:

4,4'-difluorobenzhydryl alcohol (365-24-2) → 1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazine (67469-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / toluene / 3.75 h / 40 - 85 °C / Large scale

2: sodium iodide / butanone / 24 h / 80 °C / Large scale

3: sodium carbonate / water; butanone / 24 h / 75 - 80 °C / Large scale

With sulfuric acid; sodium carbonate; sodium iodide; In water; toluene; butanone;

DOI:10.1021/op020211j

upstream raw materials:

2-[bis(4-fluorophenyl)methoxy]ethyl iodide

1-Bromo-3-phenylpropane

1-(3-phenylpropyl)piperazine

4,4'-difluorobenzhydryl alcohol

Downstream raw materials:

1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride

Refernces