N-Methyldesloratadine

Base Information

• Chemical Name: N-Methyldesloratadine
• CAS No.: 38092-89-6
• Molecular Formula: C20H21ClN2
• Molecular Weight: 324.853
• Hs Code.: 2933399090
• European Community (EC) Number: 641-012-1,923-094-3
• UNII: 70V8053T5G
• DSSTox Substance ID: DTXSID40191502
• Nikkaji Number: J1.329.319H
• Wikidata: Q27265894
• ChEMBL ID: CHEMBL420316
• Mol file: 38092-89-6.mol

Synonyms:38092-89-6;8-Chloroazatadine;N-Methyldesloratadine;N-Methyl Desloratadine;8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;8-chloro-11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;Loratadine EP Impurity G;Loratadine impurity G [EP];CHEMBL420316;UNII-70V8053T5G;MFCD06411084;70V8053T5G;8-Chloro-11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridine;13-chloro-2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene;5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-;8-chloro-11-(1-methylpiperidin-4-ylidene)-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine;8-Chloro azatadine;8-Chloro-5,6-dihydro-11H-benzo[5,6]Cyclohepto[1,2-b]pyridine-11-one;SCHEMBL4460572;DTXSID40191502;BCP31809;BDBM50031228;STL481882;AKOS005216035;DS-7427;8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;AC-26333;SY110869;LORATADINE IMPURITY G [EP IMPURITY];CS-0151108;FT-0671893;LORATADINE EP IMPURITY G (USP RC B);A856099;Q27265894;11-(1-Methylpiperidine-4-ylidene)-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine;13-chloro-2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8]pentadeca-1(11),3(8),4,6,12,14-hexaene;5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-, (Z)-2-butenedioate (1:1);8-chloro-6,11-dihydro- 11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine

Chemical Property of N-Methyldesloratadine

Chemical Property:

• Appearance/Colour: Red oil
• Vapor Pressure: 3.64E-09mmHg at 25°C
• Melting Point: 106-109 °C
• Refractive Index: 1.622
• Boiling Point: 474.3 °C at 760 mmHg
• PKA: 8.67±0.20(Predicted)
• Flash Point: 240.7 °C
• PSA: 16.13000
• Density: 1.205 g/cm³
• LogP: 4.29900
• Storage Temp.: -20?C Freezer
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 324.1393264
• Heavy Atom Count: 23
• Complexity: 451

Purity/Quality:

99%, ^*data from raw suppliers

8-Chloro-6- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
• Uses: An intermediate in the synthesis of Loratadine. Loratadine impurity. N-Methyl Desloratadine (Loratadine EP Impurity G; Loratadine USP Related Compound B) is an intermediate in the synthesis of Loratadine. Loratadine impurity.

Technology Process of N-Methyldesloratadine

There total 16 articles about N-Methyldesloratadine 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: 91.0%

1-(METHYL-4-PIPERIDINYL)[3-(2-(3-CHLORO-PHENYL)ETHYL)-2-PYRIDINYL]METHANONE HYDROCHLORIDE (119770-60-4,107256-31-5) → N-methyldesloratadine (38092-89-6)

Guidance literature:

With hydrogen fluoride; boron trifluoride; at -35 ℃;

DOI:10.1021/jo00270a041

Reference yield: 91.0%

→ N-methyldesloratadine (38092-89-6)

Guidance literature:

Reference yield: 85.0%

8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol (38089-93-9) → N-methyldesloratadine (38092-89-6)

Guidance literature:

With sulfuric acid; at 20 ℃; for 4.5h;

DOI:10.1016/j.bmcl.2012.03.002

upstream raw materials:

methanesulfonic acid

1-(METHYL-4-PIPERIDINYL)[3-(2-(3-CHLORO-PHENYL)ETHYL)-2-PYRIDINYL]METHANONE HYDROCHLORIDE

{3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone

2-cyano-3-methylpyridine

Downstream raw materials:

descarboethoxyloratadine

N-formyldesloratadine

N-acetyl desloratadine

(4-(8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)piperidin-1-yl)(phenyl)methanone

Refernces

• 1、 Cuboni, Serena,Devigny, Christian,Hoogeland, Bastiaan,Strasser, Andrea,Pomplun, Sebastian,Hauger, Barbara,H?fner, Georg,Wanner, Klaus T.,Eder, Matthias,Buschauer, Armin,Holsboer, Florian,Hausch, Felix. "Loratadine and analogues: Discovery and preliminary structure-activity relationship of inhibitors of the amino acid transporter B0AT2". supporting information. p. 9473 - 9479. Retrieved 2015/01/09.
• 2、 -. "A PROCESS FOR THE MANUFACTURING OF LORATADINE AND ITS INTERMEDIATES". Page/Page column 17. . Retrieved 2010/02/15.