21091-60-1

Basic information

• Product Name: 2-(4-BENZYLPIPERAZIN-1-YL)METHOXYBENZENE
• Synonyms: 2-(4-BENZYLPIPERAZIN-1-YL)METHOXYBENZENE
• CAS NO: 21091-60-1
• Molecular Formula: C₁₈H₂₂N₂O
• Molecular Weight: 282.38
• Mol File: 21091-60-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 413.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.107±0.06 g/cm3(Predicted)
• PKA: 7.62±0.10(Predicted)
• CAS DataBase Reference: 2-(4-BENZYLPIPERAZIN-1-YL)METHOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BENZYLPIPERAZIN-1-YL)METHOXYBENZENE(21091-60-1)
• EPA Substance Registry System: 2-(4-BENZYLPIPERAZIN-1-YL)METHOXYBENZENE(21091-60-1)

Safety Data

• Hazardous Substances Data: 21091-60-1(Hazardous Substances Data)

Usage

Chemical structure

Consists of a benzene ring with a methoxy group and a piperazine ring with a benzyl group.

Usage

Commonly used in the synthesis of pharmaceuticals, particularly in the development of antipsychotic and antidepressant drugs.

Potential therapeutic applications

Has been investigated for its potential in treating neurological disorders and substance abuse.

Interactions with brain receptors

Studied for its interactions with serotonin and dopamine receptors in the brain.

Pharmacological properties

Demonstrated promising pharmacological properties and is an important molecule in medicinal chemistry research.

Upstream product

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• 115755-27-6 4-benzyl-1-(2-methoxyphenyl)piperazine-2,6-dione 
• 100-39-0 benzyl bromide 
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• 115755-26-5 1-(2-methoxyphenyl)piperazine-2,6-dione 
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Relevant articles and documents

Interaction of arylpiperazines with the dopamine receptor D2 binding site

The docking of several 1-benzyl-4-arylpiperazines to the dopamine receptor (DAR) D2 was examined. The results demonstrated that the interaction of protonated N1 of the piperazine ring with Asp 86 (III.32) and edge-to-face interactions of the aromatic ring of the arylpiperazine part of the ligand with Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) of the receptor, represent the major stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could build one more hydrogen bond with Trp 182 (VI.48). Bulky substituents in position 4 were not tolerated due to the unfavorable sterical interaction with Phe 178 (VI.44). Substituents in position 2 and 3 were found to be sterically well tolerated. Introduction of electron attractive -NO2 group in position 3 of arylpiperazines decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity comparing to that of the phenylpiperazine 1. This can be explained in terms of favoured edge-to-face interactions in ligands with a high negative electrostatic surface potential (ESP) in the centre of aromatic residue of arylpiperazines. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands to form complexes with the DAR D2. Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) can be considered as a part of the ancillary DAR D2 pocket preserved in most G protein-coupled receptors of the A class and obviously, the arylpiperazine structural motif represents one of the privileged structures that bind to this pocket.

Direct Substitution of Aromatic Ethers by Lithium Amides. A New Aromatic Amination Reaction

Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution.Especially with lithiated secondary amines high conversions and selectivities are achieved.Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates.The scope and mechanistic implications of this novel nucleophilic amination reaction are described.

Potential antihypertensive agents. II. Unsymmetrically 1,4-disubstituted piperazines.

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