1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE

Base Information

• Chemical Name: 1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE
• CAS No.: 131779-46-9
• Molecular Formula: C₁₆H₂₁N₃O₂S
• Molecular Weight: 319.428
• Mol file: 131779-46-9.mol

Synonyms:1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE

Chemical Property of 1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE

Chemical Property:

• PSA: 73.91000
• LogP: 3.35630
• Solubility.: DCM

Purity/Quality:

99%min ^*data from raw suppliers

4-(1,2-Benzisothiazol-3-yl)-1-piperazinecarboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(1,2-Benzisothiazol-3-yl)-1-piperazinecarboxylic Acid 1,1-Dimethylethyl Ester is an intermediate in the synthesis of Ziprasidone (Z485010) related compounds.

Technology Process of 1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE

There total 3 articles about 1,1-DIMETHYLETHYL 4-(1,2-BENZISOTHIAZOLE-3-YL)-1-PIPERAZINECARBOXYLATE 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%

di-tert-butyl dicarbonate (24424-99-5) + 3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) → 1,1-dimethylethyl 4-(1,2-benzisothiazol-3-yl)-1-piperazinecarboxylate (131779-46-9)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1021/jm00115a024

Reference yield: 73.0%

3-hydroxy-4-(4-boc-piperazinyl)-1,2,5-thiadiazole + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 1,1-dimethylethyl 4-(1,2-benzisothiazol-3-yl)-1-piperazinecarboxylate (131779-46-9)

Guidance literature:

With cesium fluoride; In tetrahydrofuran; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02347

Reference yield:

4-(4-chloro-[1,2,5]thiadiazol-3-yl)piperazine-1-carboxylic acid tert-butyl ester (291748-19-1) → 1,1-dimethylethyl 4-(1,2-benzisothiazol-3-yl)-1-piperazinecarboxylate (131779-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / water; dimethyl sulfoxide / 4 h / Inert atmosphere; Reflux

2: cesium fluoride / tetrahydrofuran / Inert atmosphere

With cesium fluoride; potassium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide;

DOI:10.1021/acs.orglett.5b02347

upstream raw materials:

di-tert-butyl dicarbonate

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

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

4-(4-chloro-[1,2,5]thiadiazol-3-yl)piperazine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Cipollina, Joseph A.,Ruediger, Edward H.,New, James S.,Wire, Mary E.,Shepherd, Timothy A.,et al.. "Synthesis and Biological Activity of the Putative Metabolites of the Atypical Antipsychotic Agent Tiospirone". . p. 3316 - 3328. Retrieved 2007/10/02.