11-Hydroxy-N-methyldesloratadine

Base Information

• Chemical Name: 11-Hydroxy-N-methyldesloratadine
• CAS No.: 38089-93-9
• Molecular Formula: C20H23ClN2O
• Molecular Weight: 342.868
• Hs Code.: 2933990090
• European Community (EC) Number: 609-518-7
• UNII: 7FN2MM460T
• DSSTox Substance ID: DTXSID301119015
• Wikidata: Q27268201
• Mol file: 38089-93-9.mol

Synonyms:38089-93-9;8-Chloro-11-(1-methylpiperidin-4-yl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol;11-Hydroxy-N-methyldesloratadine;8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-B]pyridin-11-ol;11-Hydroxy-N-methyl Dihydro Loratadine;Desloratadine 11-hydroxy-N-methyl;UNII-7FN2MM460T;(+/-)-11-Hydroxy-N-methyldesloratadine;7FN2MM460T;13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol;EC 609-518-7;(11RS)-8-Chloro-11-hydroxy-11-(1-methylpiperidin-4-yl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;5H-Benzo(5,6)cyclohepta(1,2-b)pyridin-11-ol, 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-;Loratadine impurity, 8-chloro-6,11-dihydro-11-(N-methyl-4-piperidinyl)11-hydroxy-5H-benzo(5,6)cyclohepta(1,2-b)pyridine- [USP];Loratadine Impurity D;5H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol, 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-;8-Chloro-11-(1-methylpiperidin-4-yl)-6,11-dihydro-5H-benzo(5,6)cyclohepta (1,2-b) pyridin-11-ol;8-chloro-11-(1-methylpiperidin-4-yl)-6,11-dihydro-5H-benzo[5,6]cyclohepta [1,2-b] pyridin-11-ol;LORATADINE IMPURITY 10;SCHEMBL4457894;HSLLZISLOQPUNP-UHFFFAOYSA-N;DTXSID301119015;BCP31811;AKOS015964678;AC-26334;CS-0451904;FT-0657832;Q27268201;11-Hydroxy N-Methyl Dihydrodesloratadine;8-Chloro-6,11-dihydro-11-[N-methyl-4 piperidinyl]-11-hydroxy-5H-benzo[5,6] cyclohepta[1,2-b]pyridine;13-chloro-2-(1-methylpiperidin-4-yl)-4-azatricyclo[9.4.0.0^{3,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ol;8-Chloro-11-(1-methyl-piperidin-4-yl)-6,11-dihydro-5hbenzo(5,6)cyclohepta(1,2-b)pyridin-11-ol

Chemical Property of 11-Hydroxy-N-methyldesloratadine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.621
• Boiling Point: 478.12 °C at 760 mmHg
• PKA: 12.25±0.20(Predicted)
• Flash Point: 242.958 °C
• PSA: 36.36000
• Density: 1.244 g/cm³
• LogP: 3.34920
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 342.1498911
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

99.9% ^*data from raw suppliers

11-Hydroxy-N-methyl dihydro loratadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(CC1)C2(C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)O
• Uses: 11-Hydroxy-N-methyl Dihydroloratadine is an impurity of Loratadine (L469575). 11-Hydroxy-N-methyl Dihydroloratadine (Loratadine USP Related Compound D) is an impurity of Loratadine (L469575).

Technology Process of 11-Hydroxy-N-methyldesloratadine

There total 3 articles about 11-Hydroxy-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: 95.0%

8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (31251-41-9) + (1-methyl-4-piperidyl)magnesium chloride (63463-36-5) → 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol (38089-93-9)

Guidance literature:

In tetrahydrofuran; Reflux;

DOI:10.1016/j.bmcl.2012.03.002

Reference yield: 73.6%

4-chloro-1-methylpiperidine (5570-77-4) + 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (31251-41-9) → 8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol (38089-93-9)

Guidance literature:

4-chloro-1-methylpiperidine; With magnesium; ethylene dibromide; In tetrahydrofuran; at 20 - 48 ℃;

8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one; In tetrahydrofuran; at -80 - -70 ℃; for 2 - 3h; Product distribution / selectivity;

Reference yield:

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

Guidance literature:

entspr. Azaketon, Grignardreagenz aus 3-Dimethylaminopropylchlorid;

DOI:10.1021/jm00277a013

upstream raw materials:

8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

(1-methyl-4-piperidyl)magnesium chloride

4-chloro-1-methylpiperidine

Downstream raw materials:

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(2-methoxyphenyl)-1-piperidinecarbothioamide

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-cyclohexyl-1-piperidinecarbothioamide

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-phenyl-1-piperidinecarbothioamide

4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-N-(2-methylphenyl)-1-piperidinecarbothioamide

Refernces

• 1、 -. "Benzocycloheptanopyridine compound, and preparation method and application thereof". Paragraph 0081. . Retrieved 2021/07/21.
• 2、 Hatano, Manabu,Ito, Orie,Suzuki, Shinji,Ishihara, Kazuaki. "Zinc(II)-catalyzed addition of grignard reagents to ketones". scheme or table. p. 5008 - 5016. Retrieved 2010/10/04.