56227-56-6

Basic information

• Product Name: 2-(4-Benzoyl-1-piperazinyl)ethanol
• Synonyms: 2-(4-Benzoyl-1-piperazinyl)ethanol
• CAS NO: 56227-56-6
• Molecular Formula: C₁₃H₁₈N₂O₂
• Molecular Weight: 234
• Mol File: 56227-56-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Benzoyl-1-piperazinyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Benzoyl-1-piperazinyl)ethanol(56227-56-6)
• EPA Substance Registry System: 2-(4-Benzoyl-1-piperazinyl)ethanol(56227-56-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 56227-56-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2-(4-Benzoyl-1-piperazinyl)ethanol is used as a research compound for exploring its potential therapeutic effects and mechanisms of action in various medical conditions.
Used in Central Nervous System Depressant Applications:
2-(4-Benzoyl-1-piperazinyl)ethanol is used as a central nervous system depressant, potentially helping to alleviate symptoms of anxiety and stress by reducing the activity of the central nervous system.
Used in Anesthetic Applications:
As an anesthetic agent, 2-(4-Benzoyl-1-piperazinyl)ethanol may be employed to induce a state of temporary loss of sensation or consciousness, facilitating medical procedures that require pain relief.
Used in Antipsychotic Applications:
2-(4-Benzoyl-1-piperazinyl)ethanol is used as an antipsychotic agent, potentially aiding in the management of psychotic disorders by influencing the activity of neurotransmitters in the brain.
Used in Treatment of Anxiety and Mood Disorders:
2-(4-Benzoyl-1-piperazinyl)ethanol may be used in the treatment of anxiety and mood disorders, potentially offering relief from symptoms by modulating the central nervous system and neurotransmitter levels.
Ongoing research is essential to assess the safety and efficacy of 2-(4-Benzoyl-1-piperazinyl)ethanol for these applications, ensuring its potential benefits can be harnessed while minimizing any adverse effects.

Upstream product

• 65-85-0 benzoic acid 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 93-89-0 benzoic acid ethyl ester 
• 56227-55-5 N-benzoylpiperazine hydrochloride 
• 540-51-2 2-bromoethanol 
• 77278-38-7 4-benzoylpiperazine-1-carboxylic acid tert-butyl ester 
• 98-88-4 benzoyl chloride 
• 37593-94-5 4-chloro-2-nitrophenyl benzoate 
• 5005-35-6 2-pyridyl benzoate 
• 36228-61-2 4-(Benzoyloxy)pyridine 
• 35539-24-3 S-2,4-dinitrophenyl thiobenzoate 
• 1219-32-5 S-4-nitrophenyl thiobenzoate 
• 13754-38-6 N-Benzoylpiperazine 
• 959-22-8 p-nitrophenylbenzoate 

Downstream Products

• 1148156-72-2 C₁₃H₁₆N₂O₂ 
• 56227-57-7 (4-(2-chloroethyl)piperazin-1-yl)(phenyl)methanone 
• 104290-56-4 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-[2-(4-benzoyl-piperazin-1-yl)-ethyl] ester 5-methyl ester 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 104329-00-2 3-Oxo-butyric acid 2-(4-benzoyl-piperazin-1-yl)-ethyl ester 

Relevant articles and documents

Design and synthesis of the 4H-chromenone derivatives against psoriasis

On basis of Quercetin moiety, two series of 20 new compounds were designed and synthesized accordingly in this study, and their anti-inflammatory activities in vitro and in vivo were evaluated. At last, compound 8A2: 3- (1- (2- (4- (5-bromo-2-chlorobenzoyl) piperazin-1-yl) ethyl)-1H-1,2,3-triazol-4-yl) methoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one with low toxicity was found the best one for inhibiting of NO. Meanwhile, this compound could significantly inhibit the expression of IL-6 (Interleukin-6), TNF-α (Tumor necrosis factor-α) and IL-17 (Interleukin-17), and also significantly down-regulate IL-17 mRNA psoriasis model in vitro. Further studies were performed to establish mouse psoriasis model induced by Imiquimod (IMQ), and the preliminary mechanism indicated that compound 8A2 may alleviate mouse psoriasis through obstructed the JAK1/2-STAT1/3 pathway. This study should be provide a basis for further study of effective treatment of psoriasis.

Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines

Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.

C-3 NOVEL TRITERPENE WITH C-17 AMINE DERIVATIVES AS HIV INHIBITORS

The present invention relates to to C-3 novel triterpene with C-17 amine derivatives of formula (I); or pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, prodrugs, compositions or combination thereof, wherein R1, R2, R3, R4, R5 and 'n' are as defined herein. The present invention also relates to pharmaceutical compositions comprising compounds of formula (I) and process for preparing them, and their use for the treatment of viral diseases and particularly HIV mediated diseases.

Kinetic study on aminolysis of 4-pyridyl benzoate and O-4-pyridyl thionobenzoate in acetonitrile: Factors influencing reactivity and reaction mechanism

A kinetic study on nucleophilic substitution reactions of 4-pyridyl benzoate (2a) andO-4-pyridyl thionobenzoate (2b) with a series of cyclic secondary amines in acetonitrile at 25.0°C is reported. Plots of pseudo-first-order rate constant (kobsd) vs. [amine] are linear and pass through the origin for the reactions of 2a but curve upward for those of 2b. The upward curvature observed for the reactions of 2b is typical for reactions that proceed through a stepwise mechanism with a zwitterionic intermediate T±, which decomposes to the products via uncatalyzed and catalyzed routes competitively. The reaction of 2a has been suggested to proceed through a stepwise mechanism with T±, in which expulsion of the leaving group occurs in the rate-determining step on the basis of a linear Br?nsted-type plot with βnuc = 0.77. The catalyzed reaction of 2b from T± has been proposed to proceed through a concerted mechanism with a six-membered cyclic transition state rather than via a stepwise pathway with an anionic intermediate T-. Factors influencing reactivity and reaction mechanism are discussed in detail.

Kinetic study on aminolysis of 2-chloro-4-nitrophenyl x-substituted-benzoates in acetonitrile and in H2O Containing 20mol% DMSO: Effects of medium and substituent X on reactivity and reaction mechanism

Second-order rate constants for reactions of 2-chloro-4-nitrophenyl X-substituted-benzoates 1a-1j with a series of cyclic secondary amines in MeCN have been measured. Comparison of the kinetic results with those reported previously for the corresponding reactions carried out in H2O containing 20 mol % DMSO has revealed that amines are less reactive in MeCN. The Bronsted-type plot for the aminolysis of 2-chloro-4-nitrophenyl benzoate (1f) in MeCN is linear with βnuc= 0.64, which is in contrast to the curved Bronsted-type plot reported for the reaction performed in the H2O-DMSO misxture. The Hammett plot for the reactions of 1a-1j with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX= 1.22 and r = 0.60, indicating that the nonlinear Hammett plot is not due to a change in rate-determining step but is caused by stabilization of substrates possessing an electron-donating substituent through resonance interactions between the substituent and the carbonyl functionality. It has been concluded that medium change from the H2O-DMSO mixture to MeCN forces the aminolysis of 1a-1j to proceed through a concerted mechanism by destabilizing the zwitterionic tetrahedral intermediate (T±).

Discovery of novel lead in the group of N-substituted piperazine ether derivatives with potential histamine H3 receptor activity

The search for novel lead from the group of various substituted N-piperazine ether derivatives was performed. Acyl- and pyridylpiperazine ethyl/propyl ethers were obtained via three different synthetic pathways. Affinity to histamine H3 receptor was established, as well as, for selected compounds, selectivity towards histamine H4R. Docking studies to the histamine H3R homology model strengthened the position of (4-(3-(4-(3-chlorobenzoyl) piperazin-1- yl)propoxy)phenyl)(cyclopropyl)methanone (compound 26) as a novel lead for further studies on histamine H3 receptor antagonist/inverse agonist.

Kinetic study on aminolysis of y-substituted-phenyl x-substituted- benzoates: Effects of substituents x and y on reactivity and reaction mechanism

A kinetic study on aminolysis of 2-chloro-4-nitrophenyl X-substituted-benzoates (2a-k) in 80 mol % H2O/20 mol % DMSO at 25.0 oC is reported. The Bronsted-type plot for the reactions of 2-chloro-4-nitrophenyl benzoate (2g) with a series of cyclic secondary amines curves downward (e.g., β1 = 0.25, β2 = 0.85 and pKa o = 10.3), which is typical of reactions reported to proceed through a stepwise mechanism with a change in ratedetermining step (RDS). The Hammett plot for the reactions of 2a-k with piperidine consists of two intersecting straight lines, while the corresponding Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.15 and r = 0.59. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in RDS but is caused by stabilization of substrates through resonance interactions between the electron-donating substituent and the C=O bond. Substrates possessing a substituent at the 2-position of the leaving aryloxide deviate negatively from the curved Bronsted-type plot for the reactions of Y-substituted-phenyl benzoates (3ai), implying that the steric hindrance exerted by the substituent at the 2-position is an important factor which governs the reactivity of Y-substituted-phenyl benzoates.

Comparison of aminolysis of 2-pyridyl and 4-pyridyl x-substituted benzoates in acetonitrile: Evidence for a concerted mechanism involving a cyclic transition state

A kinetic study on reactions of 2-pyridyl X-substituted benzoates (6a-i) with a series of cyclic secondary amines in MeCN is reported. The Hammett plot for the reaction of 6a-i with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.28 and r = 0.63, indicating that the nonlinear Hammett plot is not caused by a change in the rate-determining step but rather by resonance stabilization of substrates possessing an electron-donating group (EDG) in the benzoyl moiety. The Bronsted-type plots are linear with βnuc = 0.59 ± 0.02, which is typical of reactions reported to proceed through a concerted mechanism. A cyclic transition state (TS), which forces the reaction to proceed through a concerted mechanism, is proposed. The deuterium kinetic isotope effect of 1.3 ± 0.1 is consistent with the proposed mechanism. Analysis of activation parameters reveals that ΔH? increases linearly as the substituent X changes from an electron-withdrawing group (EWG) to an EDG, while TΔS ? remains nearly constant with a large negative value. The constant TΔS? value further supports the proposal that the reaction proceeds through a concerted mechanism with a cyclic TS.

Kinetic study on aminolysis of 4-pyridyl X-substituted benzoates: Effect of substituent X on reactivity and reaction mechanism

A kinetic study is reported for nucleophilic substitution reactions of 4-pyridyl X-substituted benzoates 7a-e with a series of alicyclic secondary amines in H2O. The Bronsted-type plot for the reactions of 4-pyridyl benzoate 7c is linear with βnuc = 0.71. The corresponding reactions of 2-pyridyl benzoate 6, which is less reactive than 7c, resulted in also a linear Bronsted-type plot with βnuc = 0.77. The fact that the more reactive 7c results in a smaller βnuc value appears to be in accord with the reactivity- selectivity principle. The aminolysis of 7c has been suggested to proceed through a stepwise mechanism in which breakdown of the intermediate is the rate-determining step (RDS). The Hammett plot for the reactions of 7a-e with piperidine consists of two intersecting straight lines, i.e., ρX = 1.47 for substrates possessing an electron-donating group (EDG) and ρX = 0.91 for those possessing an electron-withdrawing group (EWG). In contrast, the corresponding Yukawa- Tsuno plot exhibits excellent linear correlation with ρX = 0.79 and r = 0.56. Thus, it has been concluded that the nonlinear Hammett plot is not due to a change in the RDS but is caused by stabilization of the ground state of the substrates possessing an EDG through resonance interaction between the EDG and the C=O bond of the substrates.

A kinetic study on aminolysis of 2-pyridyl X-substituted benzoates: Effect of changing leaving group from 4-nitrophenolate to 2-pyridinolate on reactivity and mechanism

Second-order rate constants (kN) have been measured spectrophotometrically for nucleophilic substitution reactions of 2-pyridyl X-substituted benzoates 8a-e with a series of alicyclic secondary amines in H2O at 25.0 ± 0.1 °C. The kN values for the reactions of 8a-e are slightly smaller than the corresponding reactions of 4-nitrophenyl X-substituted benzoates 1a-e (e.g., kN 1a-e/kN8a-e = 1.1 3.1), although 2-pyridinolate in 8a-e is ca. 4.5 pKa units more basic than 4-nitrophenolate in 1a-e. The Bronsted-type plot for the aminolysis of 8c (X = H) is linear with βnuc = 0.77 and R2 = 0.991 (Figure 1), which is typical for reactions reported previously to proceed through a stepwise mechanism with breakdown of a zwitterionic tetrahedral intermediate T± being the rate-determining step (RDS), e.g., aminolysis of 4-nitrophenyl benzoate 1c. The Hammett plot for the reactions of 8a-e with piperidine consists of two intersecting straight lines (Figure 2), i.e., ρ = 1.71 for substrates possessing an electron-donating group (EDG) while ρ = 0.86 for those bearing an electron-withdrawing group (EWG). Traditionally, such a nonlinear Hammett plot has been interpreted as a change in RDS upon changing substituent X in the benzoyl moiety. However, it has been proposed that the nonlinear Hammett is not due to a change in RDS since the corresponding Yukawa-Tsuno plot exhibits excellent linear correlation with ρ = 0.85 and r = 0.62 (R2 = 0.995, Figure 3). Stabilization of substrates 8a-e in the ground state has been concluded to be responsible for the nonlinear Hammett plot.