74852-62-3

Basic information

• Product Name: 1-(4-AMINOPHENYL)-4-(4-METHOXYPHENYL)PIPERAZINE
• Synonyms: AKOS B033041;4-[4-(4-METHYLOXY-PHENYL)-PIPERAZIN-1-YL]-PHENYLAMINE;1-(4-METHOXYPHEAYL)-4-(4-AMINOPHENYL)PIPERAZINE;1-(4-METHOXYPHENYL)-4-(4-AMINOPHENYL)PIPERAZINE;1-(4-AMINOPHENYL)-4-(4-METHOXYPHENYL)PIPERAZINE;1-(4-METHOXYPHEAYL)-4-(4-AMINOPHENGL)PIPERAZINE;4-[4-(4-Methoxyphenyl)-1-piperazinyl]benzenaMine;1-(4-Aminophenyl)-4-(4-methoxyphenyl)piperazine, 4-[4-(4-Aminophenyl)piperazin-1-yl]anisole
• CAS NO: 74852-62-3
• Molecular Formula: C₁₇H₂₁N₃O
• Molecular Weight: 283.37
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74852-62-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 506.7 ºC at 760 mmHg
• Flash Point: 260.3 ºC
• Appearance: purple solid
• Density: 1.165 g/cm³
• Vapor Pressure: 2.16E-10mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• PKA: 7.69±0.10(Predicted)
• CAS DataBase Reference: 1-(4-AMINOPHENYL)-4-(4-METHOXYPHENYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-AMINOPHENYL)-4-(4-METHOXYPHENYL)PIPERAZINE(74852-62-3)
• EPA Substance Registry System: 1-(4-AMINOPHENYL)-4-(4-METHOXYPHENYL)PIPERAZINE(74852-62-3)

Safety Data

• Hazardous Substances Data: 74852-62-3(Hazardous Substances Data)

Usage

Chemical Properties

Purple Solid

Uses

4-[4-(4-Methyloxy-phenyl)-piperazin-1-yl]-phenylamine, is an intermediate for the synthesis of Itraconazole (I937500), an Antifungal.

InChI:InChI=1/C17H21N3O/c1-21-17-8-6-16(7-9-17)20-12-10-19(11-13-20)15-4-2-14(18)3-5-15/h2-9H,10-13,18H2,1H3

Upstream product

• 74852-61-2 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-piperazine 
• 106-39-8 bromochlorobenzene 
• 3367-54-2 N,N'-di(p-chlorophenyl)piperazine 
• 100-00-5 4-chlorobenzonitrile 
• 38212-30-5 4-(4-methoxyphenyl)piperazine 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 74853-08-0 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine 
• 219923-93-0 N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]urea 
• 847951-97-7 N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-N'-propylurea 
• 74852-90-7 2,4-dihydro-4-{4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl}-5-methyl-3H-1,2,4-triazol-3-one 
• 74853-06-8 phenyl (4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate 
• 106461-41-0 (-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one 
• 252964-68-4 2-(sec-butyl)-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1242155-80-1 4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenylisocyanate 
• 89848-52-2 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isobutyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-48-6 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-5-methyl-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-51-1 2-Butyl-4-[4-(4-{4-[(2R,4S)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-50-0 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isopropyl-5-methyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-53-3 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-isobutyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 89848-47-5 4-[4-(4-{4-[(2R,4S)-2-(2,4-Dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-propyl-2,4-dihydro-[1,2,4]triazol-3-one 

Relevant articles and documents

Preparation method of posaconazole intermediate 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine

The invention discloses a preparation method of a posaconazole intermediate, namely 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine, belonging to the field of medicinal chemistry. The preparation method comprises the following steps: S1, with chlorobromobenzene and anhydrous piperazine as raw materials, generating 1,4-bis(4-chlorophenyl)piperazine under certain conditions; S2, performing single-side methylation on the product generated in the step S1 to obtain 1-(4-methoxyphenyl)-4-(4-chlorophenyl)piperazine; S3, performing ammoniation on the product in the step S2 to obtain 1-(4-methoxyphenyl)-4-(4-aminophenyl)piperazine; and S4, demethylating the product obtained in the step S3, and carrying out crystallizing and purifying to obtain the 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine.The raw materials used in the preparation method are very cheap; reaction conditions are relatively simple; the method is easy to implement; yield is high; and the cost of a final product can be obviously reduced.

Design and synthesis of some new 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-ureas as potent anticonvulsant and antidepressant agents

A series of 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-urea derivatives (29–42) were designed, synthesized and evaluated for their anticonvulsant activity by using maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure tests. The acute neurotoxicity was checked by rotarod assay. Most of the test compounds were found effective in both seizure tests. Compound 30 (1-{4-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-urea) exhibited marked anticonvulsant activity in MES as well as scPTZ tests. The phase II anticonvulsant quantification study of compound 30 indicates the ED50value of 28.5?mg/kg against MES induced seizures. In addition, this compound also showed considerable protection against pilocarpine induced status epilepticus in rats. Seizures induced by 3-mercaptopropionic acid model and thiosemicarbazide were significantly attenuated by compound 30, which suggested its broad spectrum of anticonvulsant activity. Interestingly, compound 30 displayed better antidepressant activity than standard drug fluoxetine. Moreover, compound 30 appeared as a non-toxic chemical entity in sub-acute toxicity studies.

Design, synthesis and pharmacological evaluation of N-[4-(4-(alkyl/aryl/heteroaryl)-piperazin-1-yl)-phenyl]-carbamic acid ethyl ester derivatives as novel anticonvulsant agents

A series of alkyl/aryl/heteroaryl piperazine derivatives (37-54) were designed and synthesized as potential anticonvulsant agents. The target compounds are endowed with satisfactory physicochemical as well as pharmacokinetic properties. The synthesized compounds were screened for their in vivo anticonvulsant activity in maximal electroshock (MES) and subcutaneous pentylenetetrazole (sc-PTZ) seizure tests. Further, neurotoxicity evaluation was carried out using rotarod method. Structure activity relationship studies showed that compounds possessing aromatic group at the piperazine ring displayed potent anticonvulsant activity. Majority of the compounds showed anti-MES activity whereas compounds 39, 41, 42, 43, 44, 50, 52, and 53 exhibited anticonvulsant activity in both seizure tests. All the compounds except 42, 46, 47, and 50 did not show neurotoxicity. The most active derivative, 45 demonstrated potent anticonvulsant activity in MES test at the dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h) and also delivered excellent protection in sc-PTZ test (100 mg/kg) at both time intervals. Therefore, compound 45 was further assessed in PTZ-kindling model of epilepsy which is widely used model for studying epileptogenesis. This compound was effective in delaying onset of PTZ-evoked seizures at the dose of 5 mg/kg in kindled animals and significantly reduced oxidative stress better than standard drug phenobarbital (PB). In result, compound 45 emerged as a most potent and safer anticonvulsant lead molecule.