943-17-9

White or almost white, crystalline powder or colourless crystals.

Circupon,Troponwerke,W. Germany

ChEBI: Etilefrine hydrochloride (TN) is a member of phenols.

30 parts of 1-(3'-hydroxyphenyl)-2-(N-benzylaminomethyl)-ethan-1-one are mixed with 100 parts of pyridine and 30 parts of pivalic anhydride and dissolved while warming. After heating for 1 hour under reflux, the acylation is complete. After concentrating the reaction solution, the product is precipitated from acetone/ether. Yield: 96.4% of 1-(3'-pivaloyloxyphenyl)-2- (N-benzylaminomethyl)-ethan-1-one.
3 parts of palladium/charcoal (10% strength) are prehydrogenated in water, thereafter 10 parts of 1-(3'-pivaloyloxyphenyl)-2-(N-benzylaminoethyl)-ethan- 1-one, dissolved in a 10-fold amount of water, are added dropwise at room temperature and hydrogenation is carried out until 1 mol of hydrogen has been taken up. After filtering off the catalyst, a further 3 parts of palladium/charcoal are added and hydrogenation is carried out until a further mol of hydrogen has been taken up. The catalyst is separated off and after removal of the solvent the hydrogenation product is reprecipitated from acetone/petroleum ether and from methanol/ether until it is pure according to thin layer chromatography. Yield: 38.8% of 1-(3'-pivaloyloxyphenyl)-2- ethylaminoethanol-1 hydroxide, melting point 208°C to 209°C.

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