Pitolisant

Base Information

• Chemical Name: Pitolisant
• CAS No.: 362665-56-3
• Molecular Formula: C17H26ClNO
• Molecular Weight: 295.853
• UNII: 4BC83L4PIY
• DSSTox Substance ID: DTXSID30957654
• Nikkaji Number: J1.574.747A
• Wikipedia: Pitolisant
• Wikidata: Q426044
• NCI Thesaurus Code: C166747
• RXCUI: 2197878
• Pharos Ligand ID: SGNUZPNGMXH7
• Metabolomics Workbench ID: 152764
• ChEMBL ID: CHEMBL462605
• Mol file: 362665-56-3.mol

Synonyms:1-(3-(3-(4-chlorophenyl)propoxy)propyl)piperidine;BF-2549;BF2.649;pitolisant;tiprolisant;Wakix

Chemical Property of Pitolisant

Chemical Property:

• Boiling Point: 398.7±32.0 °C(Predicted)
• PKA: 9.41±0.10(Predicted)
• PSA: 12.47000
• Density: 1.056
• LogP: 4.10310
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 295.1702921
• Heavy Atom Count: 20
• Complexity: 235

Purity/Quality:

99.0% ^*data from raw suppliers

Pitolisant >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: CNS Drugs
• Canonical SMILES: C1CCN(CC1)CCCOCCCC2=CC=C(C=C2)Cl
• Recent ClinicalTrials: A Clinical Study to Evaluate the Efficacy and Safety of Pitolisant in the Treatment of EDS in Patients With OSA
• Recent EU Clinical Trials: A Multisite Randomized, Double-Blind, Placebo-Controlled Trial
• Uses: Pitolisant is a potent and selective nonimidazole inverse agonist at the recombinant human histamine H3 receptor. Pitolisant is also used in the treatment of patients with narcolepsy, excessive daytime sleepiness, cataplexy, disturbed nocturnal sleep, hypnagogic hallucinations and sleep paralysis

Technology Process of Pitolisant

There total 5 articles about Pitolisant 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: 99.3%

3-piperidinopropan-1-ol (104-58-5) + methanesulfonic acid 3-(4-chlorophenyl)-propyl ester (61440-60-6) → pitolisant (362665-56-3)

Guidance literature:

3-piperidinopropan-1-ol; With sodium hydride; In ISOPROPYLAMIDE; at 50 ℃; for 1h;

methanesulfonic acid 3-(4-chlorophenyl)-propyl ester; In ISOPROPYLAMIDE; at 22 - 25 ℃; for 9h;

Reference yield: 75.0%

sodium 3-piperidinopropanolate (462115-38-4) + methanesulfonic acid 3-(4-chlorophenyl)-propyl ester (61440-60-6) → pitolisant (362665-56-3)

Guidance literature:

15-crown-5; In toluene; for 4h; Heating / reflux;

Reference yield:

N-(3-chloropropyl)-piperidine (1458-63-5) + 3-(p-chlorophenyl)propanol (6282-88-8) → pitolisant (362665-56-3)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 95 ℃; for 12h;

upstream raw materials:

3-piperidinopropan-1-ol

methanesulfonic acid 3-(4-chlorophenyl)-propyl ester

sodium 3-piperidinopropanolate

N-(3-chloropropyl)-piperidine

Refernces

• 1、 -. "PROCESS FOR PREPARING 1-[3-[3-(4-CHLOROPHENYL)PROPOXY]PROPYL]-PIPERIDINE". Page/Page column 4-5. . Retrieved 2010/11/25.
• 2、 Meier,Apelt,Reichert,Grassmann,Ligneau,Elz,Leurquin,Ganellin,Schwartz,Schunack,Stark. "Influence of imidazole replacement in different structural classes of histamine H3-receptor antagonists". . p. 249 - 259. Retrieved 2007/10/03.