Piperaquine

Base Information

• Chemical Name: Piperaquine
• CAS No.: 4085-31-8
• Deprecated CAS: 83764-65-2
• Molecular Formula: C29H32Cl2N6
• Molecular Weight: 535.519
• Hs Code.: 2942000000
• UNII: A0HV2Q956Y
• DSSTox Substance ID: DTXSID00193825
• Nikkaji Number: J126.229G
• Wikipedia: Piperaquine
• Wikidata: Q7197338
• NCI Thesaurus Code: C87634
• Pharos Ligand ID: XZWZZFX4VFLM
• Metabolomics Workbench ID: 154681
• ChEMBL ID: CHEMBL303933
• Mol file: 4085-31-8.mol

Synonyms:1,3-bis(1-(7-chloro-4'-quinolyl)-4'-piperazinyl)propane;piperaquine;piperaquine phosphate;piperaquine phosphate (1:1);piperaquine phosphate (1:4) anhydrous;piperaquine tetraphosphate anhydrous;piperaquine tetraphosphate tetrahydrate;quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-);quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-, phosphate (1:1);quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-, phosphate (1:4);quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-, phosphate, hydrate (1:4:4)

Chemical Property of Piperaquine

Chemical Property:

• Appearance/Colour: Almost wite powder
• Melting Point: 198-200 °C
• Boiling Point: 721.1 °C at 760 mmHg
• PKA: 8.92±0.50(Predicted)
• Flash Point: 389.9 °C
• PSA: 38.74000
• Density: 1.292 g/cm³
• LogP: 5.42990
• Solubility.: ≤0.2mg/ml in DMSO
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 534.2065504
• Heavy Atom Count: 37
• Complexity: 655

Purity/Quality:

99%min ^*data from raw suppliers

PiperaquinePhosphate >99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCN1CCCN2CCN(CC2)C3=C4C=CC(=CC4=NC=C3)Cl)C5=C6C=CC(=CC6=NC=C5)Cl
• Recent ClinicalTrials: Momordica Charantia and Dihydroartemisinin-piperaquined-primaquine for Uncomplicated Plasmodium Falciparum Malaria Patients in Southwest Sumba Regency
• Recent EU Clinical Trials: Controlled Human Malaria Infection study to assess gametocytaemia and mosquito transmissibility in participants challenged with Plasmodium falciparum by sporozoite challenge to establish a model for the evaluation of transmission-blocking interventions

Technology Process of Piperaquine

There total 3 articles about Piperaquine 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:

1,3-dibromo-propane (109-64-8) + 7-chloro-4-piperazinylquinoline (837-52-5) → 1,3-bis[1-(7-chloroquinolin-4-yl)piperazin-4-yl]propane (4085-31-8,83764-65-2)

Guidance literature:

With sodium carbonate; In water; at 100 ℃; for 15h;

Reference yield:

4,7-dichloroquinoline (86-98-6,1138471-54-1) → 1,3-bis[1-(7-chloroquinolin-4-yl)piperazin-4-yl]propane (4085-31-8,83764-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium iodide / isopropyl alcohol / 10 h / Reflux; Heating

2: triethylamine / methanol / Heating; Reflux

With triethylamine; potassium iodide; In methanol; isopropyl alcohol;

Reference yield:

→ 1,3-bis[1-(7-chloroquinolin-4-yl)piperazin-4-yl]propane (4085-31-8,83764-65-2)

Guidance literature:

resp. Amin, resp. Halogenid;

upstream raw materials:

1,3-dibromo-propane

7-chloro-4-piperazinylquinoline

4,7-dichloroquinoline

Downstream raw materials:

Piperaquine tetraphosphate

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

Refernces

• 1、 -. "PREPARATION OF BISQUINOLINE COMPOUNDS". Page/Page column 3. . Retrieved 2008/06/13.