Aripiprazole N4-Oxide

Base Information

• Chemical Name: Aripiprazole N4-Oxide
• CAS No.: 573691-11-9
• Molecular Formula: C₂₃H₂₇Cl₂N₃O₃
• Molecular Weight: 464.392
• DSSTox Substance ID: DTXSID00436567
• Wikidata: Q82251855
• Mol file: 573691-11-9.mol

Synonyms:Aripiprazole N4-Oxide;573691-11-9;Aripiprazole-d8N4-Oxide;7-[4-[4-(2,3-dichlorophenyl)-4-oxidopiperazin-4-ium-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one;Aripiprazole Impurity 9;DTXSID00436567;FT-0662282

Chemical Property of Aripiprazole N4-Oxide

Chemical Property:

• Melting Point: >149°C (dec.)
• PSA: 74.49000
• LogP: 4.98080
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 463.1429471
• Heavy Atom Count: 31
• Complexity: 603

Purity/Quality:

> 95% ^*data from raw suppliers

Aripiprazole N4-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC2=C1C=CC(=C2)OCCCCN3CC[N+](CC3)(C4=C(C(=CC=C4)Cl)Cl)[O-]
• Uses: A metabolite of anti-psychotic drug, Aripiprazole (A771000). Aripiprazole N4-Oxide is a metabolite of anti-psychotic drug, Aripiprazole (A771000). Aripiprazole Impurity 9

Technology Process of Aripiprazole N4-Oxide

There total 5 articles about Aripiprazole N4-Oxide 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: 58.3%

1-(2,3-dichloro-phenyl)-piperazine 1-oxide (902456-05-7) + 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone (129722-34-5) → 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl (4-N-oxo)]butoxy}3,4-dihydro-2(1H)-quinolinone (573691-11-9)

Guidance literature:

With triethylamine; In methanol; for 30h; Heating;

DOI:10.1515/HC.2005.11.6.485

Reference yield:

[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-phenyl-methanone (902456-03-5) → 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl (4-N-oxo)]butoxy}3,4-dihydro-2(1H)-quinolinone (573691-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 65.9 percent / m-chloro perbenzoic acid / CH₂Cl₂

2: 73.8 percent / H₂SO₄ / H₂O / 30 h / 50 - 60 °C

3: 58.3 percent / Et₃N / methanol / 30 h / Heating

With sulfuric acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water;

DOI:10.1515/HC.2005.11.6.485

Reference yield:

[4-(2,3-dichloro-phenyl)-4-oxy-piperazin-1-yl]-phenyl-methanone (902456-04-6) → 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl (4-N-oxo)]butoxy}3,4-dihydro-2(1H)-quinolinone (573691-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73.8 percent / H₂SO₄ / H₂O / 30 h / 50 - 60 °C

2: 58.3 percent / Et₃N / methanol / 30 h / Heating

With sulfuric acid; triethylamine; In methanol; water;

DOI:10.1515/HC.2005.11.6.485

upstream raw materials:

1-(2,3-dichloro-phenyl)-piperazine 1-oxide

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-phenyl-methanone

[4-(2,3-dichloro-phenyl)-4-oxy-piperazin-1-yl]-phenyl-methanone

Refernces