7-Chloro-4-(piperazin-1-yl)quinoline

Base Information

• Chemical Name: 7-Chloro-4-(piperazin-1-yl)quinoline
• CAS No.: 837-52-5
• Molecular Formula: C13H14 Cl N3
• Molecular Weight: 247.727
• Hs Code.: 2933990090
• European Community (EC) Number: 877-908-6
• UNII: 9JZN0X101D
• DSSTox Substance ID: DTXSID50353336
• Nikkaji Number: J528.747B
• Wikidata: Q72457760
• Pharos Ligand ID: 93FCXLG44ZTY
• ChEMBL ID: CHEMBL236696
• Mol file: 837-52-5.mol

Synonyms:7-chloro-4-(piperazin-1-yl)quinoline;837-52-5;7-Chloro-4-piperazinoquinoline;7-Chloro-4-piperazin-1-yl-quinoline;7-Chloro-4-piperazinylquinoline;7-chloro-4-piperazin-1-ylquinoline;7-chloro-4-(1-piperazinyl)quinoline;Quinoline, 7-chloro-4-(1-piperazinyl)-;MLS000049580;Chloroquinolinylpiperazine;MFCD01476123;9JZN0X101D;7-chloranyl-4-piperazin-1-yl-quinoline;SMR000076122;(7-chloro-4-quinolyl)piperazine;1-(7-Chloroquinolin-4-yl)piperazine;UNII-9JZN0X101D;Oprea1_754690;CHEMBL236696;cid_738389;SCHEMBL2253710;7-chloro-4-piperazino-quinoline;BDBM56192;DTXSID50353336;DNXNPMDUDGUXOB-UHFFFAOYSA-N;HMS1699O08;HMS2368H05;1-(7-chloro-4-quinolyl)piperazine;STK171908;AKOS000200388;DS-0497;FS-2848;HY-W020111;SDCCGMLS-0012643.P002;7-chloro-4-(piperazin-1-yl)-quinoline;7-chloro-4-(piperazine-1-yl)quinoline;PD158357;SY017765;AM20061869;BB 0216369;CS-0034950;FT-0621386;EN300-29379;7-chloro-4-piperazin-1-yl-quinoline, AldrichCPR;A840644;J-519209;BRD-K55354661-001-04-2;Z57394156

Chemical Property of 7-Chloro-4-(piperazin-1-yl)quinoline

Chemical Property:

• Appearance/Colour: light yellow Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 113-116ºC
• Boiling Point: 433.5 °C at 760 mmHg
• PKA: 8.62±0.50(Predicted)
• Flash Point: 216 °C
• PSA: 28.16000
• Density: 1.257 g/cm₃
• LogP: 2.69160
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 247.0876252
• Heavy Atom Count: 17
• Complexity: 255

Purity/Quality:

99%, ^*data from raw suppliers

7-Chloro-4-(piperazin-1-yl)quinoline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xi,Xn
• Statements: 34-22
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=C3C=CC(=CC3=NC=C2)Cl
• Uses: 7-Chloro-4-(piperazin-1-yl)quinoline is a metabolite of Piperaquine phosphate (P480050), a low toxicity and quick acting antimalarial drug that is used to treat malaria.

Technology Process of 7-Chloro-4-(piperazin-1-yl)quinoline

There total 5 articles about 7-Chloro-4-(piperazin-1-yl)quinoline 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: 100.0%

piperazine (110-85-0) + 4,7-dichloroquinoline (86-98-6,1138471-54-1) → 7-chloro-4-piperazinylquinoline (837-52-5)

Guidance literature:

In isopropyl alcohol; at 100 ℃; for 20h;

DOI:10.1016/j.ejmech.2021.113330

Reference yield:

3-chloro-aniline (108-42-9) → 7-chloro-4-piperazinylquinoline (837-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 4 h / 110 °C

2: dowtherm / 4 h

3: trichlorophosphate / 6 h / Reflux

4: isopropyl alcohol / 16 h / Inert atmosphere

With trichlorophosphate; In isopropyl alcohol;

DOI:10.1016/j.bmcl.2018.11.002

Reference yield:

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5) → 7-chloro-4-piperazinylquinoline (837-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dowtherm / 4 h

2: trichlorophosphate / 6 h / Reflux

3: isopropyl alcohol / 16 h / Inert atmosphere

With trichlorophosphate; In isopropyl alcohol;

DOI:10.1016/j.bmcl.2018.11.002

upstream raw materials:

piperazine

4,7-dichloroquinoline

3-chloro-aniline

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester

Downstream raw materials:

1,3-bis[1-(7-chloroquinolin-4-yl)piperazin-4-yl]propane

Refernces

• 1、 Chiyanzu, Idan,Clarkson, Cailean,Smith, Peter J.,Lehman, Julie,Gut, Jiri,Rosenthal, Philip J.,Chibale, Kelly. "Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives". . p. 3249 - 3261. Retrieved 2005.
• 2、 Singh, Anju,Kalamuddin, Md,Maqbool, Mudasir,Mohmmed, Asif,Malhotra, Pawan,Hoda, Nasimul. "Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies". supporting information. . Retrieved 2020/12/07.
• 3、 Solbak, Sara Marie ?ie,Zang, Jie,Narayanan, Dilip,H?j, Lars Jakobsen,Bucciarelli, Saskia,Softley, Charlotte,Meier, Sebastian,Langkilde, Annette Eva,Gotfredsen, Charlotte Held,Sattler, Michael,Bach, Anders. "Developing Inhibitors of the p47phox-p22phox Protein-Protein Interaction by Fragment-Based Drug Discovery". . p. 1156 - 1177. Retrieved 2020/03/10.