Loratadine ketone

Base Information

• Chemical Name: Loratadine ketone
• CAS No.: 130642-50-1
• Molecular Formula: C20H23 Cl N2 O
• Molecular Weight: 342.868
• Hs Code.: 2933990090
• Mol file: 130642-50-1.mol

Synonyms:(1-Methyl-4-piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2-pyridinyl]methanone

Chemical Property of Loratadine ketone

Chemical Property:

• Melting Point: 179-186 ºC
• Boiling Point: 462.0±45.0 °C(Predicted)
• PKA: 8.18±0.10(Predicted)
• PSA: 33.20000
• Density: 1.169±0.06 g/cm3(Predicted)
• LogP: 3.98260

Purity/Quality:

99% ^*data from raw suppliers

[3-[2-(3-Chlorophenyl)ethyl]-2-pyridinyl](1-methyl-4-piperidinyl)methanone(LoratadineKetoneImpurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: [3-[2-(3-Chlorophenyl)ethyl]-2-pyridinyl](1-methyl-4-piperidinyl)methanone is an impurity of Loratadine (L469575), a nonsedating-type histamine H1-receptor.

Technology Process of Loratadine ketone

There total 4 articles about Loratadine ketone 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:

3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile (31255-57-9) + (1-methyl-4-piperidyl)magnesium chloride (63463-36-5) → {3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone (130642-50-1)

Guidance literature:

With hydrogenchloride; Multistep reaction; 1.) THF, reflux;

DOI:10.1021/jm00105a069

Reference yield:

N-tert-butyl-3-methylpyridine-2-carboxamide (32998-95-1) → {3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone (130642-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, -40 deg C

2: POCl₃ / Heating

3: 2.) aq. HCl / 1.) THF, reflux

With hydrogenchloride; n-butyllithium; trichlorophosphate;

DOI:10.1021/jm00105a069

Reference yield:

3-<2-(3-chlorophenyl)ethyl>-N-(1,1-dimethylethyl)-2-pyridinecarboxamide (107285-30-3) → {3-[2-(3-Chloro-phenyl)-ethyl]-pyridin-2-yl}-(1-methyl-piperidin-4-yl)-methanone (130642-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: POCl₃ / Heating

2: 2.) aq. HCl / 1.) THF, reflux

With hydrogenchloride; trichlorophosphate;

DOI:10.1021/jm00105a069

upstream raw materials:

3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile

(1-methyl-4-piperidyl)magnesium chloride

N-tert-butyl-3-methylpyridine-2-carboxamide

3-<2-(3-chlorophenyl)ethyl>-N-(1,1-dimethylethyl)-2-pyridinecarboxamide

Downstream raw materials:

loratadine

N-acetyl desloratadine

N-formyldesloratadine

descarboethoxyloratadine

Refernces

• 1、 Piwinski, John J.,Wong, Jesse K.,Green, Michael J.,Ganguly, Ashit K.,Billah, M. Motasim,et al.. "Dual Antagonists of Platelet Activating Factor and Histamine. Identification of Structural Requirements for Dual Activity of N-Acyl-4-(5,6-dihydro-11H-benzocycloheptapyridin-11-ylidene)piperidines". . p. 457 - 461. Retrieved 2007/10/02.