Rupatadine

Base Information

• Chemical Name: Rupatadine
• CAS No.: 158876-82-5
• Molecular Formula: C26H26ClN3
• Molecular Weight: 415.966
• Hs Code.: 2933990090
• European Community (EC) Number: 825-304-8
• UNII: 2AE8M83G3E
• DSSTox Substance ID: DTXSID00166534
• Nikkaji Number: J602.046A
• Wikipedia: Rupatadine
• Wikidata: Q423450
• NCI Thesaurus Code: C73055
• Pharos Ligand ID: F9AYB5KBYU5V
• Metabolomics Workbench ID: 152745
• ChEMBL ID: CHEMBL91397
• Mol file: 158876-82-5.mol

Synonyms:8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine;rupatadine;UR 12592;UR-12592

Chemical Property of Rupatadine

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 9.83E-14mmHg at 25°C
• Melting Point: 58-61 °C
• Boiling Point: 586.4 °C at 760 mmHg
• PKA: 6.95±0.20(Predicted)
• Flash Point: 308.4 °C
• PSA: 29.02000
• Density: 1.233 g/cm³
• LogP: 5.57280
• Solubility.: Dichloromethane; Ethyl Acetate
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 415.1815255
• Heavy Atom Count: 30
• Complexity: 609

Purity/Quality:

99% ^*data from raw suppliers

8-Chloro-11-(1-((5-methylpyridin-3-yl)methyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CN=C1)CN2CCC(=C3C4=C(CCC5=C3N=CC=C5)C=C(C=C4)Cl)CC2
• Recent ClinicalTrials: A Comparative Study of Rupatadine 10 mg Tablets and Clarinex? 5 mg Tablets Under Fasting Conditions
• Recent EU Clinical Trials: A Randomised, Double-blind, Two-arm, Parallel Groups, Multicentre Study to evaluate the efficacy and safety of a Fixed Dose Combination of Rupatadine and Montelukast vs. Rupatadine in adult patients with Seasonal Allergic Rhinitis with and without mild to moderate Bronchial Asthma
• Recent NIPH Clinical Trials: PRIME study
• Uses: Rupatadine Fumarate is a dual antagonist of histamine H1 and platelet-activating factor receptors. Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. Rupatadine is an intermediate in the synthesis of Rupatadine (5-Methyl-3-pyridinyl)methyl)pyridinium Chloride (M326740). (5-Methy-3-pyridinyl)methyl-Rupatadine is an impurity of Rupatadine (R701650), a dual antagonist of histamine H1 and platelet-activating factor receptors

Technology Process of Rupatadine

There total 11 articles about Rupatadine 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: 89.8%

3-(chloromethyl)-5-methylpyridine hydrogen chloride (1007089-84-0) + descarboethoxyloratadine (100643-71-8) → rupatadine (158876-82-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 20h; Temperature; Concentration; Inert atmosphere;

Reference yield: 67.66%

3-bromo-5-methylpyridine hydrochloride (182354-92-3) + descarboethoxyloratadine (100643-71-8) → rupatadine (158876-82-5)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; water; at 0 - 20 ℃; for 13h; Product distribution / selectivity;

Reference yield: 40.0%

→ rupatadine (158876-82-5)

Guidance literature:

upstream raw materials:

3-(bromomethyl)-5-methylpyridine

descarboethoxyloratadine

3-(chloromethyl)-5-methylpyridine hydrogen chloride

3,5-Lutidine

Refernces

• 1、 -. "An improved process for the preparation of Rupatadine Fumarate". . . Retrieved 2015/02/02.
• 2、 Agarwal, Rajendra,Bhirud, Shekhar Bhaskar,Bijukumar, Gopinathenpillai,Khude, Gopal Dnyandev. "Expedient synthesis of rupatadine". . p. 122 - 127. Retrieved 2008/03/14.