Vilazodone hydrochloride

Base Information

• Chemical Name: Vilazodone hydrochloride
• CAS No.: 163521-08-2
• Molecular Formula: C₂₂H₃₆O₄
• Molecular Weight: 364.525
• Hs Code.: 29329990
• European Community (EC) Number: 695-883-8
• UNII: U8HTX2GK8J
• DSSTox Substance ID: DTXSID80936833
• Wikidata: Q27139037
• NCI Thesaurus Code: C90717
• RXCUI: 1086768
• ChEMBL ID: CHEMBL1615374
• Mol file: 163521-08-2.mol

Synonyms:2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1);5-(4-(4-(5-cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide;68843, EMD;EMB 68843;EMB-68843;EMB68843;EMD 68843;HCl, Vilazodone;Hydrochloride, Vilazodone;Viibryd;vilazodone;Vilazodone HCl;vilazodone hydrochloride

Chemical Property of Vilazodone hydrochloride

Chemical Property:

• Appearance/Colour: White to almost white powder
• Melting Point: 279°C(lit.)
• Boiling Point: 745.1 °C at 760 mmHg
• Flash Point: 404.4 °C
• PSA: 103.28000
• LogP: 5.71868
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble20mg/mL, clear
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 477.1931528
• Heavy Atom Count: 34
• Complexity: 729

Purity/Quality:

99% ^*data from raw suppliers

Vilazodone hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N.Cl
• Recent EU Clinical Trials: A Multicenter, Randomized, Double-Blind, Placebo-Controlled, Relapse Prevention Study with Vilazodone in Patients with Major Depressive Disorder
• Description: Vilazodone is a selective serotonin reuptake inhibitor (SSRI) and a partial agonist of the serotonin (5-HT) receptor subtype 5-HT1A (IC50s = 0.2 and 0.5 nM, respectively). It increases extracellular 5-HT in the rat ventral hippocampus and frontal cortex when administered intraperitoneally at doses of 1 and 3 mg/kg. Vilazodone (1 mg/kg, i.p.) decreases immobility in the forced swim test in both rats and mice. Formulations containing vilazodone have been used in the treatment of depression.
• Uses: Vilazodone Hydrochloride, is the salt form of Vilazodone (V265000), which is a combined serotonin specific reuptake inhibitor (SSRI) and 5-HT1A receptor partial agonist currently under clinical evaluation for the treatment of major depression. Antidepressant.
• Clinical Use: Althoughseveral synthetic approaches have beenreported,a process-scale synthesis of vilazodone consists of the union of an indole-containing butyl tosylate 284 with a benzofuranyl piperazine whose synthesis is described in the scheme below. Piperazine 280 arises from a Buchwald coupling of commercially available benzofuranyl bromide 279 with piperazine through the use of a unique catalyst system employing the DavePhos ligand. This single coupling step, which has been executed on multigram scale in 70% yield,210 circumvented the need for any protecting group chemistry for either the primary amide within 279 or the piperazine amine functionality. For the preparation of the key indole subunit, Friedel-Crafts acylation of commercially available 5-cyanoindole (281) proceeded in good yield at the 3-position of the indole with 4-chlorobutanoyl chloride in 82% yield. Treatment of the resulting chloroketone with sodium borohydride in refluxing isopropanol converted 282 to the corresponding terminal alcohol 283. Tosylation of this alcohol was followed by displacement with piperazine 280 to give vilazodone hydrochloride (XXV) after acidification.

Technology Process of Vilazodone hydrochloride

There total 11 articles about Vilazodone hydrochloride 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:

3β,11α-diacetoxy-17-hydroxy-16α-methyl-5α-pregnan-20-one (13263-45-1) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1002/hlca.19590420636

Reference yield:

3β,11α-diacetoxy-5α-pregn-16-en-20-one (28507-80-4) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: CuCl / anschliessende Acetylierung

2: monoperoxyphthalic acid; diethyl ether / Erwaermen des Reaktionsprodukts mit wss.-methanol.K₂CO₃ und Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Pyridin

3: methanol; sodium methylate

With methanol; monoperoxyphthalic acid; diethyl ether; sodium methylate; copper(l) chloride;

DOI:10.1002/hlca.19590420636

Reference yield:

(17Ξ)-3β,11α,20-triacetoxy-16α-methyl-5α-pregn-17(20)-ene (810-38-8) → 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one (1635-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: monoperoxyphthalic acid; diethyl ether / Erwaermen des Reaktionsprodukts mit wss.-methanol.K₂CO₃ und Behandeln des danach isolierten Reaktionsprodukts mit Acetanhydrid und Pyridin

2: methanol; sodium methylate

With methanol; monoperoxyphthalic acid; diethyl ether; sodium methylate;

DOI:10.1002/hlca.19590420636

upstream raw materials:

3β,11α-diacetoxy-17-hydroxy-16α-methyl-5α-pregnan-20-one

3β,11α-diacetoxy-5α-pregn-16-en-20-one

(17Ξ)-3β,11α,20-triacetoxy-16α-methyl-5α-pregn-17(20)-ene