270062-75-4

Basic information

• Product Name: 1-(4-nitrobenzyl)-4-(2-methoxyphenyl)piperazine
• Synonyms: 1-(4-nitrobenzyl)-4-(2-methoxyphenyl)piperazine
• CAS NO: 270062-75-4
• Molecular Weight: 327.383
• Mol File: 270062-75-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(4-nitrobenzyl)-4-(2-methoxyphenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-nitrobenzyl)-4-(2-methoxyphenyl)piperazine(270062-75-4)
• EPA Substance Registry System: 1-(4-nitrobenzyl)-4-(2-methoxyphenyl)piperazine(270062-75-4)

Safety Data

• Hazardous Substances Data: 270062-75-4(Hazardous Substances Data)

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 5464-78-8 1-(2-methoxyphenyl)piperazine hydrochloride 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 

Downstream Products

• 70261-72-2 4-[[4-[[4-(4-methoxyphenyl)-1-piperazinyl ]-methyl ]phenyl ]amino ]-7-(trifluoromethyl)-quinoline 
• 70261-78-8 1-(4-methoxyphenyl)-4-[ (4-aminophenyl)-methyl ]piperazine 

Relevant articles and documents

The Effect of Carboxamide/Sulfonamide Replacement in Arylpiperazinylalkyl Derivatives on Activity to Serotonin and Dopamine Receptors

A series of carboxamide and sulfonamide alkyl (p-xylyl and benzyl) 1-(2-methoxyphenyl)piperazine (o-OMe-PhP) and 1-(2,3-dichlorophenyl)piperazine (2,3-DCPP) analogs were prepared and tested for their affinity to bind to serotonin 5-HT1A/5-HT6/5-HT7 and dopamine D2 receptors. This chemical modification let us explore the impact of the replacement of the carboxamide by the sulfonamide group on the affinity changes. In both the o-OMe-PhP and 2,3-DCPP series, the relative activities of the carboxamides versus sulfonamides toward the 5-HT1A/5-HT6/5-HT7 and D2 receptors show similar trends. Varied or similar activities for particular receptors were found for the carboxamides/sulfonamides with p-xylyl spacer, while of the two classes of carboxamides and sulfonamides examined, benzyl derivatives of the sulfonamides displayed the highest serotoninergic affinity, in particular to the 5-HT7 receptors (Ki 8–85 nM). The Ki values revealed that, irrespective of the carboxamide/sulfonamide zone, both p-xylyl and benzyl derivatives had the highest affinity for the dopamine D2 receptor (i.e., 16 out of 24 compounds investigated have an affinity below 100 nM). A molecular modeling study of carboxamide 9a and sulfonamide 9b showed that their binding effects to each of 5-HT1AR and D2R created binding modes interaction with different conserved receptors residues. Structural similarities of carboxamide 9a in complexes with a 5-HT1AR (9aI) and D2R (9aII) are over 83%, while the respective similarities of sulfonamide 9b structures (9bI/9bII) are only about 40%.

Thin layer chromatography as a tool for reaction optimisation in microwave assisted synthesis

Reaction parameters for the microwave assisted synthesis of N'- substituted arylpiperazines were optimised via their rapid synthesis on thin layer chromatography (TLC) plates.