50606-33-2

Usage

Role in organic synthesis

Building block 1-Piperazinecarboxylic acid, phenyl ester is commonly used as a fundamental component in the synthesis of various pharmaceuticals and biologically active compounds.

Application in medicinal chemistry

Synthesis of pharmaceuticals 1-Piperazinecarboxylic acid, phenyl ester is used to create drugs for various medical conditions, particularly those related to central nervous system disorders.

Potential use in agrochemicals

Pest control and crop protection 1-Piperazinecarboxylic acid, phenyl ester can be utilized in the development of chemicals for agricultural purposes, such as controlling pests and protecting crops.

Upstream product

• 110-85-0 piperazine 
• 64897-42-3 phenyl 2,4-dinitrophenyl carbonate 
• 1885-14-9 phenyl chloroformate 
• 1170292-50-8 phenyl (2,4,6-trinitrophenyl) carbonate 
• 128337-08-6 phenyl-(2-pyridyl)carbonate 

Downstream Products

• 132019-64-8 4-[3-(5,11-Dihydro-10-thia-dibenzo[a,d]cyclohepten-5-ylcarbamoyl)-propyl]-piperazine-1-carboxylic acid phenyl ester 
• 480991-46-6 C₃₁H₃₅N₅O₆ 
• 1391636-63-7 C₂₂H₂₅ClN₂O₄ 
• 1260098-95-0 4-(2-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2-oxo-ethyl)-piperazine-1-carboxylic acid phenyl ester 
• 1392831-54-7 phenyl 4-(indoline-1-carbonyl)piperazine-1-carboxylate 
• 1392831-57-0 [4-(indoline-1-carbonyl)piperazin-1-yl](indolin-1-yl)methanone 
• 1392831-29-6 4-(imidazole-1-carbonyl)piperazine-1-carboxylic acid phenyl ester 
• 508233-74-7 vortioxetine 
• 960203-42-3 4-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine-1-carboxylic acid tert-butyl ester 
• 494773-35-2 4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester 
• 1011-13-8 1-(2-bromophenyl)piperazine 

Relevant academic research and scientific papers

A benzo [b] thiophene preparation method and intermediate

The invention provides a preparation method for benzo[b]thiophene. The preparation method comprises the following steps: substitution; ring closure; hydrolysis; decarboxylation; etc. The method effectively reduces generation of by-products, improves reaction yield, avoids usage of expensive reagents, decreases total cost and is applicable to industrial production. The invention further provides a novel compound. The novel compound is a key intermediate for preparation of benzo[b]thiophene and has a structure as shown in a formula 3 which is described in the specification. The invention also provides a preparation method for the compound 3, and the method has high yield and is simple to operate.

Kinetic study on aminolysis of phenyl 2-pyridyl carbonate in acetonitrile: Effect of intramolecular h-bonding interaction on reactivity and reaction mechanism

Second-order rate constants (kN) have been measured spectrophotometrically for the reactions of phenyl 2- pyridyl carbonate (6) with a series of cyclic secondary amines in MeCN at 25.0 ± 0.1 °C. The Bronsted-type plot for the reaction of 6 is linear with βnuc = 0.54, which is typical for reactions reported previously to proceed through a concerted mechanism. Substrate 6 is over 103 times more reactive than 2-pyridyl benzoate (5), although the reactions of 6 and 5 proceed through the same mechanism. A combination of steric hindrance, inductive effect and resonance contribution is responsible for the kinetic results. The reactions of 6 and 5 proceed through a cyclic transition state (TS) in which H-bonding interactions increase the nucleofugality of the leaving group (i.e., 2-pyridiniumoxide). The enhanced nucleofugality forces the reactions of 6 and 5 to proceed through a concerted mechanism. In contrast, the corresponding reaction of 4-nitrophenyl 2-pyridyl carbonate (7) proceeds through a stepwise mechanism with quantitative liberation of 4-nitrophenoxide ion as the leaving group, indicating that replacement of the 4-nitrophenoxy group in 7 by the PhO group in 6 changes the reaction mechanism (i.e., from a stepwise mechanism to a concerted pathway) as well as the leaving group (i.e., from 4-nitrophenoxide to 2-pyridiniumoxide). The strong electron-withdrawing ability of the 4- nitrophenoxy group in 7 inhibits formation of a H-bonded cyclic TS. The presence or absence of a H-bonded cyclic TS governs the reaction mechanism (i.e., a concerted or stepwise mechanism) as well as the leaving group (i.e., 2-pyridiniumoxide or 4-nitrophenoxide).

Concerted aminolysis of diaryl carbonates: Kinetic sensitivity on the basicity of the nucleophile, nonleaving group, and nucleofuge

The kinetics of the reactions of 4-methylphenyl, phenyl, and 4-chlorophenyl 2,4,6-trinitrophenyl carbonates (1, 2, and 3, respectively) with a series of anilines and secondary alicyclic (SA) amines has been carried out spectrophotometrically in 44 wt% ethanol-water, at 25.0°C, ionic strength 0.2 M. The BrAnsted plots (statistically corrected) for the reactions of carbonates 1-3 with anilines and SA amines were linear with slopes (βN) in the range of 0.69-0.78 and 0.45-0.48, respectively, attributed to a concerted mechanism. The negative values found for the sensitivity of log kN to the basicity of the nonleaving (βnlg) and leaving (βlg) groups are discussed. Anilines are more reactive than isobasic SA amines, probably because of the greater steric hindrance offered by the latter.

Substituted phenoxypropyl-(R)-2-methylpyrrolidine aminomethyl ketones as histamine-3 receptor inverse agonists

Optimization of a series of aminomethyl ketone diamine H3R antagonists to reduce the brain exposure by lowering the pKa, led to molecules with improved pharmacokinetic properties. Compounds 9, 19, and 25 had high affinity for human H3R and demonstrated in vivo H3R functional activity in the rat dipsogenia model. Compound 9 displayed modest wake-promoting activity in the rat EEG/EMG model.

Unsymmetrical tetrasubstituted ureas from tertiary carbamoylimidazole: Activation by AlMe3

An efficient and general method for the synthesis of unsymmetrical tetrasubstituted ureas from carbamoylimidazole is described. The conversion is achieved by the concurrent quarternization of the imidazole nitrogen and activation of amines with AlMe3. The Royal Society of Chemistry 2012.

ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

Kinetics and mechanism of the aminolysis of methyl 4-nitrophenyl, methyl 2,4-dinitrophenyl, and phenyl 2,4-dinitrophenyl carbonates

The reactions of methyl 4-nitrophenyl carbonate (MNPC) with a series of secondary alicyclic amines (SAA) and quinuclidines (QUIN), methyl 2,4-dinitrophenyl carbonate (MDNPC) with QUIN and 1-(2-hydroxyethyl)piperazinium ion (HPA), and phenyl 2,4-dinitrophenyl carbonate (PDNPC) with SAA are subjected to a kinetic investigation in aqueous solution, at 25.0°C and an ionic strength of 0.2 M. By following spectrophotometrically the nucleofuge release (330-400 nm) under amine excess, pseudo-first-order rate coefficients (kobsd) are obtained. Plots of kobsd VS [amine] at constant pH are linear, with the slope (kN) being pH independent. The Broensted-type plot (log kN vs amine pKa) for the reactions of SAA with MNPC is biphasic with slopes β1 = 0.3 (high pKa region) and β2 = 1.0 (low pKa region) and a curvature center at pKa0 = 9.3. This plot is consistent with a stepwise mechanism through a zwitterionic tetrahedral intermediate (T±) and a change in the rate-determining step with SAA basicity. The Broensted plot for the quinuclidinolysis of MNPC is linear with slope βN = 0.86, in line with a stepwise process where breakdown of T± to products is rate limiting. A previous work on the reactions of SAA with MDNPC was revised by including the reaction of HPA. The Broensted plots for the reactions of QUIN and SAA with MDNPC and SAA with PDNPC are linear with slopes β = 0.51, 0.48, and 0.39, respectively, consistent with concerted mechanisms. Since quinuclidines are better leaving groups from T± than isobasic SAA, yielding a less stable T±, it seems doubtful that the quinuclidinolysis of PDNPC is stepwise, as reported.