21279-77-6

Basic information

• Product Name: 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE
• Synonyms: 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE;1-(3-CHLORO-PROPYL)-4-(2-METHOXY-PHENYL)-PIPERAZINE;1-(3-CHLOROPROPYL)-4-(2-METHOXYPHENYL)-PIPERAZINE 2 HCL;1-(3-CHLOROPROPYL)-4-(2-METHOXYPHENYL)PIPERAZINE DIHYDROCHLORIDE;1-(3-CHLOROPROPYL)-4-(2-METHOXYPHENYL) PIPERAZINE HYDROCHLORIDE;RARECHEM AH CK 0073;1-(2-Methoxyphenyl)-4-(3-chloropropyl)-piperazine dihydrocholride;1-(3-Chloropropyl)-4-(2-methoxyphenyl)piperazineHCl
• CAS NO: 21279-77-6
• Molecular Formula: C₁₄H₂₁ClN₂O
• Molecular Weight: 341.7
• Mol File: 21279-77-6.mol

Chemical Properties

• Melting Point: 225°C (dec.)
• Boiling Point: 392.9°Cat760mmHg
• Flash Point: 191.4°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 2.21E-06mmHg at 25°C
• PKA: 7.28±0.10(Predicted)
• CAS DataBase Reference: 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE(21279-77-6)
• EPA Substance Registry System: 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE(21279-77-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 21279-77-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE is used as an intermediate in the synthesis of various pharmaceuticals due to its chemical properties that facilitate the creation of diverse medicinal compounds.
Used in Neurological and Psychiatric Treatment:
In the field of medicine, 1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE is utilized for its potential therapeutic effects in treating neurological and psychiatric disorders, leveraging its psychoactive and anxiolytic properties to alleviate symptoms and improve patient outcomes.
Used in Medical Imaging:
1-(2-METHOXYPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE DIHYDROCHLORIDE is employed as a radiotracer in positron emission tomography (PET) imaging, allowing for the diagnosis and monitoring of certain diseases by providing detailed images of biological processes in the body.

InChI:InChI=1/C14H21ClN2O.ClH/c1-18-14-6-3-2-5-13(14)17-11-9-16(10-12-17)8-4-7-15;/h2-3,5-6H,4,7-12H2,1H3;1H

Upstream product

• 5464-78-8 1-(2-methoxyphenyl)piperazine hydrochloride 
• 35386-24-4 1-(2-Methoxyphenyl)piperazine 
• 41103-43-9 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-propanol 
• 6940-76-7 1-iodo-3-chloro-propane 
• 95520-98-2 tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate 
• 109-70-6 1.3-chlorobromopropane 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 91532-13-7 3-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propyl}-3H-benzo[d][1,2,3]triazin-4-one 
• 326497-42-1 2-{3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-propyl}-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione 
• 1149351-79-0 2,3,4,5-tetrahydro-N-[3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl]benzo[c]azepin-1-one 
• 1149351-73-4 3,4-dihydro-N-[3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl]isoquinolin-1(2H)-one 
• 1186236-58-7 1‐(3‐azidopropyl)‐4‐(2‐methoxyphenyl)piperazine 

Relevant articles and documents

Leveraging a Low-Affinity Diazaspiro Orthosteric Fragment to Reduce Dopamine D3 Receptor (D3R) Ligand Promiscuity across Highly Conserved Aminergic G-Protein-Coupled Receptors (GPCRs)

Previously, we reported a 3-(2-methoxyphenyl)-9-(3-((4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio)propyl)-3,9-diazaspiro[5.5]undecane (1) compound with excellent dopamine D3 receptor (D3R) affinity (D3R Ki = 12.0 nM) and selectivity (D2R/D3R ratio = 905). Herein, we present derivatives of 1 with comparable D3R affinity (32, D3R Ki = 3.2 nM, D2R/D3R ratio = 60) and selectivity (30, D3R Ki = 21.0 nM, D2R/D3R ratio = 934). Fragmentation of 1 revealed orthosteric fragment 5a to express an unusually low D3R affinity (Ki = 2.7 μM). Compared to piperazine congener 31, which retains a high-affinity orthosteric fragment (5d, D3R Ki = 23.9 nM), 1 was found to be more selective for the D3R among D1- and D2-like receptors and exhibited negligible off-target interactions at serotoninergic and adrenergic G-protein-coupled receptors (GPCRs), common off-target sites for piperazine-containing D3R scaffolds. This study provides a unique rationale for implementing weakly potent orthosteric fragments into D3R ligand systems to minimize drug promiscuity at other aminergic GPCR sites.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

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Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis

Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

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Discovery of aryl-piperidine derivatives as potential antipsychotic agents using molecular hybridization strategy

Schizophrenia is a chronic, disabling mental disorder that affects about one percent of world's population. Drugs acting on multiple targets have been demonstrated to provide superior efficacy in schizophrenia than agents acting on single target. In this study, based on FW01, a selective potent 5-HT1A receptor agonist discovered via dynamic pharmacophore-based virtual screening, molecular hybridization strategy was employed to optimize its in vitro activity over D2 and 5-HT2A receptors. The optimized compound 9f was found to show dual potent D2 and 5-HT2A receptors antagonistic activity. In addition, compound 9f showed good in vivo metabolic stability with t1/2 of 2 h in ICR mice and good capability to penetrate the blood-brain barrier with Kp value of 4.03. These results demonstrated that the dual D2 and 5-HT1A receptor antagonist 9f could serve as a promising lead compound to discover potent antipsychotic agents.

Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols

Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.

Development of a Focused Library of Triazole-Linked Privileged-Structure-Based Conjugates Leading to the Discovery of Novel Phenotypic Hits against Protozoan Parasitic Infections

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Design, synthesis, and biological evaluation of arylpiperazine-benzylpiperidines with dual serotonin and norepinephrine reuptake inhibitory activities

The limitations of established serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake inhibitors necessitate the development of safer and more effective therapeutic agents. Based on the structures of 4-benzylpiperidine carboxamides and trazodone, arylpiperazine-benzylpiperidines with chemical scaffolds different from those of marketed drugs were designed, synthesized, and evaluated for their neurotransmitter reuptake inhibitory activities. The majority of the synthesized compounds showed greater NE than 5-HT reuptake inhibition. The activities were even greater than those of the standard drug, venlafaxine hydrochloride were. The derivatives with a three-carbon linker showed better activities than the derivatives with a two-carbon linker. Among the newly synthesized compounds, 2d exhibited the strongest reuptake inhibition of the neurotransmitters (IC50 = 0.38 μM for NE and 1.18 μM for 5-HT). The biological activity data demonstrate that arylpiperazine-benzylpiperidines have the potential to be developed as a new class of therapeutic agents to treat neuropsychiatric and neurodegenerative disorders.

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