91646-45-6

Basic information

• Product Name: 1-[4-(2-AMINOPHENYL)PIPERAZIN-1-YL]ETHANONE
• Synonyms: 2-(4-Acetyl-piperazin-1-yl)aniline;1-Acetyl-4-(2-aMinophenyl)piperazine
• CAS NO: 91646-45-6
• Molecular Formula: C₁₂H₁₇N₃O
• Molecular Weight: 219.29
• Mol File: 91646-45-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 130-131 °C
• Boiling Point: 427.3°C at 760 mmHg
• Flash Point: 212.2°C
• Appearance: /
• Density: 1.177g/cm³
• Vapor Pressure: 1.66E-07mmHg at 25°C
• Refractive Index: 1.596
• PKA: 6.91±0.10(Predicted)
• CAS DataBase Reference: 1-[4-(2-AMINOPHENYL)PIPERAZIN-1-YL]ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(2-AMINOPHENYL)PIPERAZIN-1-YL]ETHANONE(91646-45-6)
• EPA Substance Registry System: 1-[4-(2-AMINOPHENYL)PIPERAZIN-1-YL]ETHANONE(91646-45-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 91646-45-6(Hazardous Substances Data)

Usage

General Description

1-[4-(2-aminophenyl)piperazin-1-yl]ethanone, also known as 2-Amino-4'-ethoxyacetophenone, is a chemical compound used in various scientific and pharmaceutical applications. It is a ketone derivative with a piperazine and an aniline functional group. 1-[4-(2-AMINOPHENYL)PIPERAZIN-1-YL]ETHANONE has been studied for its potential pharmacological properties and has been found to exhibit promising anxiolytic and antidepressant effects. It may also have applications in the treatment of disorders such as schizophrenia and obsessive-compulsive disorder. Additionally, 1-[4-(2-aminophenyl)piperazin-1-yl]ethanone has been investigated for its potential role as a building block in the synthesis of biologically active molecules, making it a valuable compound in the field of medicinal chemistry.

InChI:InChI=1/C12H17N3O/c1-10(16)14-6-8-15(9-7-14)12-5-3-2-4-11(12)13/h2-5H,6-9,13H2,1H3

Upstream product

• 170017-73-9 1-[1,1-Dimethylethoxycarbonyl]-4-(2-nitrophenyl)piperazine 
• 13889-98-0 N-acetylpiperidine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 59084-06-9 1-(2-nitrophenyl)piperazine 
• 100138-76-9 1-(4-(2-nitrophenyl)piperazin-1-yl)ethanone 

Downstream Products

• 508233-74-7 vortioxetine 
• 960203-27-4 Vortioxetine hydrobromide 
• 150557-82-7 1-(4-(2-chlorophenyl)piperazin-1-yl)ethan-1-one 

Relevant articles and documents

Synthesis and structure-activity relationships of new 2-phenoxybenzamides with antiplasmodial activity

The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for their in vitro activity against blood stages of the NF54 strain of P. falciparum. Several insights into structure-activity relationships were revealed. The antiplasmodial activity and cytotoxicity of compounds strongly depended on the substitution pattern of the anilino partial structure as well as on the size of substituents. The diaryl ether partial structure had further impacts on the activity. Additionally, several physicochemical and pharmacokinetic parameters were calculated (log P, log D7.4 and ligand efficiency) or determined experimentally (passive permeability and CYP3A4 inhibition). The tert-butyl-4-{4-[2-(4-fluorophenoxy)-3-(trifluoromethyl)benzamido]phenyl}piperazine-1-carboxylate possesses high antiplasmodial activity against P. falciparum NF54 (PfNF54 IC50 = 0.2690 μM) and very low cytotoxicity (L-6 cells IC50 = 124.0 μM) resulting in an excellent selectivity index of 460. Compared to the lead structure 1 the antiplasmodial activity was improved as well as the physicochemical and some pharmacokinetic parameters.

SYNTHESIS OF VORTIOXETINE VIA (2-(PIPERAZINE-1 -YL)PHENYL)ANILINE INTERMEDIATES

The present invention provides a new synthetic process for the production of 1-(2-((2,4- dimethylphenyl)thio)phenyl)piperazine (vortioxetine), a drug for the treatment of depression and anxiety, which is conducted via (2-(piperazine-1-yl)phenyl)aniline intermediates.