1-(3-Chlorophenyl)piperazine hydrochloride

Base Information

• Chemical Name: 1-(3-Chlorophenyl)piperazine hydrochloride
• CAS No.: 51639-49-7
• Molecular Formula: C₁₀H₁₃ClN₂*2ClH
• Molecular Weight: 269.601
• Hs Code.: 2933599090
• European Community (EC) Number: 235-976-9,265-718-0
• NSC Number: 134746
• UNII: 7IM2GS7ILV
• DSSTox Substance ID: DTXSID40896823
• Wikidata: Q27268361
• ChEMBL ID: CHEMBL1256321
• Mol file: 51639-49-7.mol

Synonyms:1-(3-chlorophenyl)piperazine;1-(3-chlorophenyl)piperazine dihydrochloride;1-(3-chlorophenyl)piperazine monohydrochloride;1-(m-chlorophenyl)piperazine;1-3-CPP;3-chlorophenylpiperazine;dihydrochloro phenyl piperazine;m-chlorophenylpiperazine;m-CPP;meta-chlorophenylpiperazine

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Chemical Property of 1-(3-Chlorophenyl)piperazine hydrochloride

Chemical Property:

• Appearance/Colour: off-white to brown-greyish powder
• Vapor Pressure: 0.000112mmHg at 25°C
• Melting Point: 210 °C
• Boiling Point: 336.4 °C at 760mmHg
• Flash Point: 157.2 °C
• PSA: 15.27000
• LogP: 3.74740
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 232.0534038
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s): T
• Hazard Codes: Xi,T,Xn
• Statements: 36/37/38-24-22
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=CC(=CC=C2)Cl.Cl
• Description: 1-(3-Chlorophenyl)piperazine (also named as meta-Chlorophenylpiperazine (mCPP)) is a piperazine derivative and it is the major metabolite of Trazodone, Nefazodone, and Etoperidone. mCPP has stimulant and hallucinogenic properties. Pharmacologically, mCPP acts as a serotonin receptor agonist, which leads to antidepressant and anxiolytic properties, as well as hallucinogenic side effects. It was developed in the late 1970s for scientific research. Since mid-2000s, it is sold as a designer drug. mCPP can be sold as “legal Ecstasy” or as a “legal high” or “Ecstasy” itself. Nevertheless, mCPP is abused by users seeking Ecstasy-like effects. The toxic effects reported for mCPP include nausea, hallucinations, headache and most frequently, anxiety.

Technology Process of 1-(3-Chlorophenyl)piperazine hydrochloride

There total 7 articles about 1-(3-Chlorophenyl)piperazine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

bis-(2-chloroethyl)amine hydrochloride (821-48-7) + 3-chloro-aniline (108-42-9) → 1-(3-chlorophenyl)piperazine hydrochloride (13078-15-4,51639-49-7,65369-76-8)

Guidance literature:

In sulfolane; at 150 ℃; for 14h;

DOI:10.1016/j.tetlet.2015.06.003

Reference yield: 78.0%

tert-butyl 4-(3-chlorophenyl)piperazine-1-carboxylate (186790-11-4) → 1-(3-chlorophenyl)piperazine hydrochloride (13078-15-4,51639-49-7,65369-76-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/acsmedchemlett.0c00422

Reference yield:

diethanolamine hydrochloride (14426-21-2) + 3-chloroaniline hydrochloride (141-85-5) → 1-(3-chlorophenyl)piperazine hydrochloride (13078-15-4,51639-49-7,65369-76-8) + N-(3-chlorophenyl)ethylenediamine hydrochloride (143745-53-3) + 4-ethyl-3-chloro-phenyl-1-piperazine hydrochloride

Guidance literature:

at 170 ℃;

upstream raw materials:

diethanolamine hydrochloride

3-chloroaniline hydrochloride

bis-(2-chloroethyl)amine hydrochloride

3-chloro-aniline

Downstream raw materials:

trazodone

Refernces

• 1、 Wang, Chao,Wang, Zeyu,Gao, Minghuan,Li, Yuelin,Zhang, Yujing,Bao, Kai,Wu, Yingliang,Guan, Qi,Zuo, Daiying,Zhang, Weige. "Design, synthesis and anticancer activity of 5-aryl-4-(4-arylpiperazine-1-carbonyl)-1,2,3-thiadiazoles as microtubule-destabilizing agents". . . Retrieved 2020/12/21.
• 2、 Wang, Chao,Li, Yuelin,Liu, Zi,Wang, Zeyu,Liu, Zihan,Man, Shuai,Zhang, Yujing,Bao, Kai,Wu, Yingliang,Guan, Qi,Zuo, Daiying,Zhang, Weige. "Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers". . p. 549 - 560. Retrieved 2021/02/05.