Ziprasidone mesylate

Base Information

• Chemical Name: Ziprasidone mesylate
• CAS No.: 199191-69-0
• Molecular Formula: C₂₁H₂₁ClN₄OS
• Molecular Weight: 412.943
• European Community (EC) Number: 638-839-5
• NSC Number: 760351
• UNII: VCY3F61S5R
• DSSTox Substance ID: DTXSID80939920
• Wikidata: Q27291762
• NCI Thesaurus Code: C48032
• RXCUI: 353116
• ChEMBL ID: CHEMBL1200997
• Mol file: 199191-69-0.mol

Synonyms:Ziprasidone mesylate;Ziprasidone mesilate;185021-64-1;Ziprasidone mesylate anhydrous;VCY3F61S5R;2H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monomethanesulfonate;5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;methanesulfonic acid;UNII-VCY3F61S5R;CP-88059-27;C21H21ClN4OS.CH4O3S;Ziprasidone (mesylate);SCHEMBL957247;CHEMBL1200997;DTXSID80939920;LOQSYPGSAZUDJZ-UHFFFAOYSA-N;HMS3264B21;Pharmakon1600-01503850;HY-14542C;NSC760351;ZIPRASIDONE MESILATE [WHO-DD];AKOS015900335;CCG-213218;AC-23355;Q27291762;2H-INDOL-2-ONE, 5-(2-(4-(1,2-BENZISOTHIAZOL-3-YL)-1-PIPERAZINYL)ETHYL)-6-CHLORO-1,3-DIHYDRO-, METHANESULFONATE (1:1)

Chemical Property of Ziprasidone mesylate

Chemical Property:

• Vapor Pressure: 1.13E-29mmHg at 25°C
• Boiling Point: 836.3 °C at 760 mmHg
• Flash Point: 459.6 °C
• PSA: 167.15000
• LogP: 4.34180
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 508.1005753
• Heavy Atom Count: 33
• Complexity: 665

Purity/Quality:

99% ^*data from raw suppliers

Ziprasidone mesylate trihydrate European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)O.C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54
• Uses: Antipsychotic (central D2and 5HT2receptor antagonist).

Technology Process of Ziprasidone mesylate

There total 33 articles about Ziprasidone mesylate 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: 92.9%

5-(2-bromoethyl)-6-chloro-1,3-dihydrooxindole + 3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With sodium carbonate; In water; acetonitrile; Solvent; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 92.0%

3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) + 6-chloro-5-(2-chloroethyl)-2-oxindole (118289-55-7) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With Morwet D₄₂₅; In water; Reflux; Inert atmosphere;

Reference yield: 92.0%

3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride (133070-64-1,144010-02-6) + 6-chloro-5-(2-chloroethyl)-2-oxindole (118289-55-7) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With Morwet D₄₂₅; In water; Product distribution / selectivity; Reflux; Inert atmosphere;

upstream raw materials:

5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one

3-(1-piperazinyl)-1,2-benzisothiazole

6-chloro-5-(2-chloroethyl)-2-oxindole

methyl 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl acetate

Downstream raw materials:

5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]-ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one hydrobromide monohydrate

Dihydroziprasidone

Ziprasidone sulfoxide

Refernces

• 1、 -. "A key intermediate for the preparation of ziprasidone". Paragraph 0131-0134. . Retrieved 2018/04/03.
• 2、 -. "Process for the Preparation of Ziprasidone". Page/Page column 5. . Retrieved 2011/01/12.