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Orciprenaline

Basic information Safety Supplier Related

Orciprenaline Basic information

Product Name:
Orciprenaline
Synonyms:
  • 5-[1-hydroxy-2-(1-methylethylamino)ethyl]benzene-1,3-diol
  • 5-(1-hydroxy-2-propan-2-ylamino-ethyl)benzene-1,3-diol
  • orciprenaline
  • 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol
  • 1,3-Benzenediol, 5-1-hydroxy-2-(1-methylethyl)aminoethyl-
  • 1,3-Benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- (9CI)
  • 3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol
  • Benzyl alcohol, 3,5-dihydroxy-a-[(isopropylamino)methyl]- (6CI, 8CI)
CAS:
586-06-1
MF:
C11H17NO3
MW:
211.26
EINECS:
209-569-1
Product Categories:
  • Orciprenaline
Mol File:
586-06-1.mol
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Orciprenaline Chemical Properties

Melting point:
100°
Boiling point:
350.94°C (rough estimate)
Density 
1.1240 (rough estimate)
refractive index 
1.5718 (estimate)
pka
9.11±0.10(Predicted)
CAS DataBase Reference
586-06-1(CAS DataBase Reference)
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Orciprenaline Usage And Synthesis

Originator

Alupent, Boehringer Ingelheim ,W. Germany ,1961

Uses

Bronchodilator.

Manufacturing Process

In an initial operation, 3,5-diacetoxyacetophenone was reacted first with bromine and then with isopropylamine to give 1-(3,5-dihydroxyphenyl)-2- isopropylaminoethanone.
59 g of 1-(3,5-dihydroxy-phenyl)-2-isopropylaminoethanone (free base) were dissolved in 590 cc of methanol, and the solution was hydrogenated in the presence of about 80 g Raney nickel at room temperature and under a pressure of 5 atm. Hydrogen absorption was terminated after a few minutes. The catalyst was separated by vacuum filtration, and the filtrate, an ethanolic solution of 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane, was admixed with the calculated amount of an alcoholic 20% sulfuric acid solution. A crystalline precipitate formed which was filtered off and washed with alcohol. For purification, the product was dissolved in water and the solution was filtered through iron-free charcoal.
Thereafter, the filtrate was evaporated to dryness in vacuo and the residue was taken up in alcohol. The crystalline precipitate which separated out after some standing was separated by vacuum filtration and washed with alcohol. After recrystallization from 90% alcohol, 61 g (83.2% of theory) of 1-(3,5- dihydroxyphenyl)-1-hydroxy-2-isopropylamino-ethane sulfate, MP 202° to 203°C, was obtained.

Therapeutic Function

Bronchodilator

Orciprenaline Preparation Products And Raw materials

Raw materials

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