Zilpaterol Hydrochloride

Base Information

• Chemical Name: Zilpaterol Hydrochloride
• CAS No.: 119520-06-8
• Molecular Formula: C₁₄H₁₉N₃O₂*ClH
• Molecular Weight: 297.785
• European Community (EC) Number: 601-619-4
• UNII: EX8IEP25JU
• ChEMBL ID: CHEMBL513390
• Wikidata: Q27277408
• Mol file: 119520-06-8.mol

Synonyms:Zilpaterol hydrochloride;119520-06-8;Zilpaterol HCl;UNII-EX8IEP25JU;EX8IEP25JU;Imidazo(4,5,1-jk)(1)benzazepin-2(1h)-one, 4,5,6,7-tetrahydro-7-hydroxy-6-((1-methylethyl)amino)-, monohydrochloride;Rac-(6R,7R)-7-hydroxy-6-(isopropylamino)-4,5,6,7-tetrahydroimidazo(4,5,1-jk)(1)benzazepin-2(1h)-one hydrochloride;(9R,10R)-9-hydroxy-10-(propan-2-ylamino)-1,3-diazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-2-one;hydrochloride;9-Hydroxy-10-(propan-2-ylamino)-1,3-diazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-2-one;1044281-58-4;trans-(+)-Zilpaterol (hydrochloride);ZILPATEROL HYDROCHLORIDE (MART.);ZILPATEROL HYDROCHLORIDE [MART.];Zilpaterol hydrochloride (relstereo);Imidazo[4,5,1-jk][1]benzazepin-2(1H)-one, 4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-, (Hydrochloride) (1:1), (6R,7R)-;SCHEMBL135498;CHEMBL513390;1117752-22-3;AMY23433;MFCD09033213;ZILPATEROL HYDROCHLORIDE [MI];AKOS015967220;ZILPATEROL HYDROCHLORIDE [GREEN BOOK];F94045;A903870;J-501696;Q27277408;(6R,7R)-6-hydroxy-7-(isopropylamino)-6,7,8,9-tetrahydro-2,9a-diazabenzo[cd]azulen-1(2H)-one hydrochloride;(9R,10R)-9-hydroxy-10-[(propan-2-yl)amino]-1,3-diazatricyclo[6.4.1.0?,??]trideca-4,6,8(13)-trien-2-one hydrochloride;Imidazo[4,5,1-jk][1]benzazepin-2(1H)-one, 4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-, monohydrochloride, (6R,7R)-rel- (9CI);Imidazo[4,5,1-jk][1]benzazepin-2(1H)-one, 4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]-, monohydrochloride, trans-;Zilmax;trans-(+/-)-Zilpaterol hydrochloride;trans-4,5,6,7-Tetrahydro-7-hydroxy-6-(isopropylamino)imidazo[4,5,1-jk]-[1]benzazepin-2(1H)-one hydrochloride

Chemical Property of Zilpaterol Hydrochloride

Chemical Property:

• PSA: 70.31000
• LogP: 2.73850
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 297.1244046
• Heavy Atom Count: 20
• Complexity: 361

Purity/Quality:

98%-102% ^*data from raw suppliers

Zilpaterol hydrochloride VETRANAL ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NC1CCN2C3=C(C1O)C=CC=C3NC2=O.Cl
• Isomeric SMILES: CC(C)N[C@@H]1CCN2C3=C([C@H]1O)C=CC=C3NC2=O.Cl
• Description: Zilpaterol is a β-adrenergic receptor agonist that putatively through activation of protein kinase A increases protein synthesis in skeletal muscle fibers, as well as reduces lipogenesis and increases lipolysis in adipose tissues. It was approved by the FDA in 2006 as a veterinary food additive for the purpose of increasing lean body weight and improving feed efficiency in commercial beef cattle.

Technology Process of Zilpaterol Hydrochloride

There total 12 articles about Zilpaterol Hydrochloride 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: 80.44%

6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one (1021987-10-9) + acetone (67-64-1) → zilpaterol hydrochloride (119520-06-8,1044281-58-4)

Guidance literature:

6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one; acetone; With acetic acid; pH=7.5;

With palladium 10% on activated carbon; hydrogen; at 30 ℃; for 4h; under 750.075 - 22502.3 Torr;

With hydrogenchloride; In ethanol; water; ethyl acetate; at 40 ℃; for 3h;

Reference yield: 54.0%

(6R,7R)-6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one (1019837-22-9) + acetone (67-64-1) → (-)-Zilpaterol hydrochloride (119520-06-8,1044281-58-4)

Guidance literature:

(6R,7R)-6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one; acetone; In methanol; at 0 ℃; for 0.166667h;

With sodium tris(acetoxy)borohydride; In methanol; at 0 - 20 ℃;

With hydrogenchloride; water;

Reference yield:

(6R,7R)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one → (-)-Zilpaterol hydrochloride (119520-06-8,1044281-58-4)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 70 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/jm801211c

upstream raw materials:

(6R,7R)-6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one

acetone

(6S,7S)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one

5,6-dihydroimidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione

Refernces

• 1、 -. "PROCESS FOR MAKING A CRYSTALLINE ZILPATEROL SALT". Page/Page column 15-16. . Retrieved 2012/03/26.
• 2、 -. "PROCESS FOR MAKING A CRYSTALLINE ZILPATEROL SALT". Page/Page column 23; 24. . Retrieved 2010/08/05.