ChemicalBook CAS DataBase List Oxymetazoline

Oxymetazoline synthesis

1synthesis methods

Product Name:Oxymetazoline
CAS Number:1491-59-4
Molecular formula:C16H24N2O
Molecular Weight:260.37

Oxymetazoline, 6-tert-butyl-3(2-imidazolin-2-ilmethyl)-2,4-dimethylphenol (11.1.39), is synthesized by chloromethylation of 6-tert-butyl-2,4-dimethylphenol and the further transformation of the resulting chloromethyl derivative (11.1.37) into a nitrile (11.1.38). The reaction of this with ethylendiamine gives oxymetazoline (11.1.39) [41,42].

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Yield:-

Reaction Conditions:

with ammonium hydroxide at 25 - 30;

Steps:

1.1
To a stirred solution of oxymetazoline hydrochloride (1.0 eq.) in water (20.0 vol), aq. ammonia solution (1.0 vol.) was added at 25-30°C and the reaction mass was stirred for 1-2 h at 25- 30°C. The solid precipitated was filtered, washed with water (5 vol.) and suck dried for 1-2 h. The wet compound was dried under vacuum at 60 - 65°C for about 16 h to afford oxymetazoline as off white solid.

References:

CELLIX BIO PRIVATE LIMITED WO2021/19350, 2021, A1 Location in patent:Paragraph 0063-0064; 0072

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