Cetirizine Ethyl Ester

Base Information

• Chemical Name: Cetirizine Ethyl Ester
• CAS No.: 246870-46-2
• Molecular Formula: C23H29ClN2O3
• Molecular Weight: 416.94096
• Hs Code.: 2933599550
• European Community (EC) Number: 808-853-8
• UNII: 58Q9ZS6YEL
• DSSTox Substance ID: DTXSID20431731
• Mol file: 246870-46-2.mol

Synonyms:Cetirizine Ethyl Ester;246870-46-2;58Q9ZS6YEL;Cetirizine Ethyl Ester (USP RC A);Ethyl 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetate;2-(2-(4-((4-Chlorophenyl)phenylmethyl)piperazin-1-yl)ethoxy)acetic acid, ethyl ester;Acetic acid, 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-, ethyl ester;(RS)-2-(2-(4-((4-Chlorophenyl)phenylmethyl)piperazin-1-yl)ethoxy)acetic acid ethyl ester oxalate;Ethyl 2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetate;ethyl 2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetate;AGN-PC-0CEFEN;UNII-58Q9ZS6YEL;SCHEMBL12288127;DTXSID20431731;WJA87046;ethyl [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate

Chemical Property of Cetirizine Ethyl Ester

Chemical Property:

• Boiling Point: 519.9±45.0 °C(Predicted)
• PKA: 6.55±0.10(Predicted)
• PSA: 42.01000
• Density: 1.170±0.06 g/cm3(Predicted)
• LogP: 3.50250
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 416.1866705
• Heavy Atom Count: 29
• Complexity: 471

Purity/Quality:

99% ^*data from raw suppliers

Cetirizine Ethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)COCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
• Uses: 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). Cetirizine Ethyl Ester is the impurity of Cetirizine(C281101), is an antihistamine used in treatment of children with chronic spontaneous urticaria.

Technology Process of Cetirizine Ethyl Ester

There total 16 articles about Cetirizine Ethyl Ester 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: 90.8%

N-(4-chlorobenzhydryl)piperazine (303-26-4) → (2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid ethyl ester (246870-46-2)

Guidance literature:

With triethylamine;

Reference yield: 90.0%

Diazoethan (1117-96-0) + cetirizine dihydrochloride (83881-52-1,130018-87-0,163837-48-7) → (2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid ethyl ester (246870-46-2)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1021/op0002951

Reference yield: 75.0%

C19H22Cl2N2 + ethyl 2-hydroxyacetate (623-50-7) → C23H29ClN2O3 (246870-46-2)

Guidance literature:

With sodium hydride; sodium iodide; In N,N-dimethyl-formamide; acetone; at 25 ℃; for 3h;

upstream raw materials:

ethyl 2-(2-bromoethoxy)acetate

1-[(S)-(4-chlorophenyl)(phenyl)methyl]piperazine

4-chlorobenzaldehyde

benzaldehyde

Refernces

• 1、 Pflum, Derek A,Krishnamurthy, Dhileepkumar,Han, Zhengxu,Wald, Stephen A,Senanayake, Chris H. "Asymmetric synthesis of cetirizine dihydrochloride". . p. 923 - 926. Retrieved 2007/10/03.
• 2、 -. "Process for the preparation of esters of [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]-ethoxy]acetic acid". . . Retrieved 2008/06/13.