Celiprolol

Base Information

• Chemical Name: Celiprolol
• CAS No.: 56980-93-9
• Molecular Formula: C20H33N3O4
• Molecular Weight: 379.5
• European Community (EC) Number: 260-497-7
• UNII: DRB57K47QC
• DSSTox Substance ID: DTXSID3020259
• Nikkaji Number: J246.148J,J11.825G
• Wikipedia: Celiprolol
• Wikidata: Q420586
• NCI Thesaurus Code: C79558
• Pharos Ligand ID: HFQ8F3CMD68T
• Metabolomics Workbench ID: 149277
• ChEMBL ID: CHEMBL27810
• Mol file: 56980-93-9.mol

Synonyms:Celiprolol;Celiprolol Hydrochloride;Celiprolol Monohydrochloride;Celiprolol, (+,-)-Isomer;Celiprolol, (R)-Isomer;Celiprolol, (S)-Isomer;Celiprolol, Monohydrochloride, (R)-Isomer;Celiprolol, Monohydrochloride, (S)-Isomer;Hydrochloride, Celiprolol;Monohydrochloride, Celiprolol;N'-(3-Acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-N,N-diethylurea;REV 5320A;REV-5320A;REV5320A;Selectol;ST 1396;ST-1396;ST1396

Chemical Property of Celiprolol

Chemical Property:

• Vapor Pressure: 1.34E-14mmHg at 25°C
• Melting Point: 110-112°
• Refractive Index: 1.545
• Boiling Point: 586.5 °C at 760 mmHg
• PKA: pKa ～9.7 (Uncertain)
• Flash Point: 308.5 °C
• PSA: 90.90000
• Density: 1.114 g/cm³
• LogP: 3.35460
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (slightly), Methanol (Slightly)
• Water Solubility.: 22.9mg/L(22.5 oC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 379.24710654
• Heavy Atom Count: 27
• Complexity: 474

Purity/Quality:

99%, ^*data from raw suppliers

Diethyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)NC1=CC(=C(C=C1)OCC(CNC(C)(C)C)O)C(=O)C
• Recent ClinicalTrials: Chronic Beta-blockade and Cardiopulmonary Exercise in COPD
• Recent EU Clinical Trials: Proof of concept study to assess the differential effects of chronic beta-blockade (celiprolol versus bisoprolol) on cardiopulmonary outcomes at rest and during exercise in chronic obstructive pulmonary disease.
• Recent NIPH Clinical Trials: Comparison of the effects of celiprolol and bisoprolol on central BP and measures of atherosclerosis in hypertensive patients.
• Uses: Celiprolol is an intermediate in the synthesis of Celiprolol Hydrochloride (C254500). Celiprolol is a cardioselective β1-adrenergic blocker. Antihypertensive, antianginal.
• Therapeutic Function: Beta-adrenergic blocker

Technology Process of Celiprolol

There total 18 articles about Celiprolol 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: 90.0%

1-{5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}ethan-1-one (56980-94-0) + N,N-diethylcarbamyl chloride (88-10-8) → celiprolol (56980-93-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 40 ℃; for 48h;

DOI:10.1021/op000297l

Reference yield: 71.2%

tert-butylamine (75-64-9) + 3-<3-Acetyl-4-(3-brom-2-hydroxy-propoxy)-phenyl>-1,1-diethylharnstoff (85045-98-3) → celiprolol (56980-93-9)

Guidance literature:

In water; for 25.5h;

Reference yield:

4-nitrophenol acetate (830-03-5) → celiprolol (56980-93-9)

Guidance literature:

Multi-step reaction with 5 steps

1: aluminum (III) chloride / nitrobenzene / 6.5 h / 20 - 140 °C

2: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 10 h / 75 °C

3: water / 12 h / 20 °C

4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr

5: triethylamine / tetrahydrofuran / 48 h / 40 °C

With aluminum (III) chloride; palladium 10% on activated carbon; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; nitrobenzene;

DOI:10.1021/op000297l

upstream raw materials:

tert-butylamine

3-<3-Acetyl-4-(3-brom-2-hydroxy-propoxy)-phenyl>-1,1-diethylharnstoff

3-(4-Ethoxy-phenyl)-1,1-diethylharnstoff

N,N-diethylcarbamyl chloride

Downstream raw materials:

(+/-)-celiprolol hydrochloride

Refernces

• 1、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.
• 2、 -. "FLUORESCENCE BASED DETECTION OF SUBSTANCES". . . Retrieved 2009/09/28.