246870-46-2

Basic information

• Product Name: Cetirizine Ethyl Ester (USP RC A)
• Synonyms: Cetirizine Ethyl Ester (USP RC A);Levocetrizine IMpurity: IMpurity A (USP);Cetirizine Ethyl Ester;Acetic acid, 2-[2-[4-[(4- chlorophenyl)phenylMethyl]-1- piperazinyl]ethoxy]-, ethyl ester;Cetirizine Related CoMpound A;(RS)-2-[2-[4-[(4-Chlorophenyl)phenylmethyl]piperazin-1-yl]ethoxy]acetic acid ethyl ester dihydrochloride;Cetirizine ethyl ester dihydrochloride;Cetirizine USP RC A
• CAS NO: 246870-46-2
• Molecular Formula: C23H29ClN2O3
• Molecular Weight: 416.94096
• Product Categories: Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 246870-46-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 519.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.170±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.55±0.10(Predicted)
• CAS DataBase Reference: Cetirizine Ethyl Ester (USP RC A)(CAS DataBase Reference)
• NIST Chemistry Reference: Cetirizine Ethyl Ester (USP RC A)(246870-46-2)
• EPA Substance Registry System: Cetirizine Ethyl Ester (USP RC A)(246870-46-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 246870-46-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 246870-46-2 differently. You can refer to the following data:
1. Cetirizine Ethyl Ester, is an intermediate for the preparation of Cetirizine (C281100), which is a nonsedating type histamine H1-receptor antagonist. It is an antihistamine used in the treatment of allergies, hay fever, angioedema, and urticaria. It is a major metabolite of Hydroxyzine (H996500).
2. Cetirizine Ethyl Ester is the impurity of Cetirizine(C281101), is an antihistamine used in treatment of children with chronic spontaneous urticaria.

Upstream product

• 303-26-4 N-(4-chlorobenzhydryl)piperazine 
• 163837-57-8 (R)-(4-chlorophenyl)(phenyl)methylamine 
• 134-85-0 4-chlorobenzophenone 
• 28022-43-7 p-chlorobenzhydrylamine 
• 555-77-1 tris-(2-chloro-ethyl)-amine 
• 102-71-6 triethanolamine 
• 623-50-7 ethyl 2-hydroxyacetate 
• 1117-96-0 Diazoethan 
• 83881-52-1 cetirizine dihydrochloride 
• 163837-58-9 1-[(S)-(4-Chloro-phenyl)-phenyl-methyl]-4-(toluene-4-sulfonyl)-piperazine 
• 439695-63-3 (R_S,S)-(1-(4-chlorophenyl)-1-phenylmethyl)-2-methylpropanesulfinamide 
• 336105-23-8 (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide 
• 163837-32-9 (S)-4-chloro-α-phenyl-benzenemethanamine 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 

Relevant articles and documents

Preparation method of levocetirizine

The invention provides a preparation method of levocetirizine. The method comprises the following steps of: the step 1, carrying out a cyclization reaction on (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine to obtain a compound represented by a formula (I); 2, performing condensation reaction of the compound shown in the formula (I) and 2-ethyl glycolate to obtain a compound shown ina formula (II); and the step 3, converting the compound shown in the formula (II) into levocetirizine. According to the preparation method, (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine are taken as the initial raw materials, and cyclization reaction, condensation reaction and hydrolysis reaction are carried out so as to obtain levocetirizine. The synthetic route provided by the invention is short, the yield is high, and experimental results show that the yield of the levocetirizine prepared by the method provided by the invention can reach 47%, and the purity can reach 99.7%.

A large-scale synthesis of enantiomerically pure cetirizine dihydrochloride using preparative chiral HPLC

Enantiomerically pure cetirizine can be prepared by preparative HPLC separation of cetirizine amide. The amide has an α value of 2.76 (USP resolution of 8.54) using a Chiralpak AD column, and 0.5 wt % of the amide (based on packing material) can be injected per run.

A process for the preparation of esters of [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]acetic acid

The invention provides a process for the preparation of esters [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid, of the formula (I) wherein X represents a halogen atom and R represents a lower alkyl group comprising reacting: (a) a co