5696-15-1

Butoxamine,SigmaAldrich

Antidiabetic; antihyperlipoproteinemic.

Butoxamine Hydrochloride is a beta-2 selective beta blocker. β2-adrenergic receptor(AR) antagonist; Antiarrhythmic;

548.0 g (2 mol) of 2,5-dimethoxy-α-bromopropiophenone was dissolved in 500 ml of acetanitrile and 365.0 g (5 mol) of t-butylamine was added. The solution was allowed to stand at room temperature for 64 h and was then diluted with 2 L of anhydrous ether. The precipitated t-butylamine hydrobromide was filtered off and washed with ether. The filtrate and washings were concentrated in vacuo using a water-bath kept at 40°C. When most of the solvent had been removed, the residual material was dissolve in cold methanol and acidified with hydrochloric acid. The solution was then taken down to dryness in vacuo on the steam bath and the 1-(2,5- dimethoxyphenyl)-2-(t-butylamino)propiophenone was obtained, melting point 175-176°C (recrystallised from an ethanol ether mixture).
The bulk of the 1-(2,5-dimethoxyphenyl)-2-(t-butylamino)propiophenone was dissolved in methanol and hydrogenated over platinum (Adams' catalyst). After removal of the catalyst, the solvent was removed in vacuo and the residual solid was dissolved in water and the solution was washed with ether.
The aqueous layer was basified (dilute sodium hydroxide solution) and the base was taken into ether. After drying over anhydrous potassium carbonate, the ether was evaporated and the base was distille at 0.3 mm pressure. So the DL-erythro 1-(2,5-dimethoxyphenyl)-2-(t-butylamino)propanol, boiling point 127-128°C was obtained.

Oral hypoglycemic, Antihyperlipidemic