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Celiprolol

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Celiprolol Basic information

Product Name:
Celiprolol
Synonyms:
  • celiptolol
  • -diethyl-
  • n’-(3-acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)phenyl)-n,n-di
  • 3-[3-acetyl-4-(2-hydroxy-3-tert-butylamino-propoxy)-phenyl]-1,1-diethyl-urea
  • CELIPROLOL
  • Celiprolol Base
  • CELIPROLOLHYDROCHLORIDE(SUBJECTTOPANTENTFREE)
  • (R,S)-Celiprolol
CAS:
56980-93-9
MF:
C20H33N3O4
MW:
379.49
EINECS:
260-497-7
Mol File:
56980-93-9.mol
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Celiprolol Chemical Properties

Melting point:
110-112°
Boiling point:
586.5±50.0 °C(Predicted)
Density 
1.114±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under Inert Atmosphere
solubility 
Chloroform (slightly), Methanol (Slightly)
pka
pKa ~9.7 (Uncertain)
form 
Solid
color 
Yellow
Water Solubility 
22.9mg/L(22.5 ºC)
CAS DataBase Reference
56980-93-9(CAS DataBase Reference)
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Celiprolol Usage And Synthesis

Originator

Selectol,Chemie Linz,Austria,1983

Uses

Celiprolol is an intermediate in the synthesis of Celiprolol Hydrochloride (C254500). Celiprolol is a cardioselective β1-adrenergic blocker. Antihypertensive, antianginal.

Definition

ChEBI: 3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea is an aromatic ketone.

Manufacturing Process

3-Acetyl-4-hydroxyaniline, in solution in pyridine, is reacted with dimethylcarbamoyl chloride at room temperature to give N-(3-acetyl-4- hydroxy)phenyl-N'-dimethylurea, which after evaporating the pyridine, taking up the residue in chloroform and evaporating the latter, is obtained in a crystalline form. Melting point: 160°-162°C. After reaction of the product in alkaline aqueous solution, with epichlorohydrin, N-[3-acetyl-4-(2',3'-epoxy)- propoxy]-phenyl-N'-dimethylurea (melting point: 98°-102°C) is obtained, and this, in turn, is reacted with excess tert-butylamine in aqueous solution at room temperature to give N-[3-acetyl-4-(3'-tert-butylamino-2'-hydroxy)- propoxy)-phenyl-N'-dimethylurea of melting point: 120°-122°C.

Therapeutic Function

Beta-adrenergic blocker

CeliprololSupplier

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