CH222739A - Process for the preparation of an aryloxy-alkylamino-butanol. - Google Patents

Description

  

  Process for the preparation of an aryloxy-alkylamino-butanol. The subject of the present additional patent is a process for the preparation of an aryloxy-alkylamino-butanol, characterized in that phenoxyacetone is reacted with formaldehyde and morpholine to give 1-phenoxy-4-morpholinylbutanone-2 and this compound is reduced to the corresponding secondary alcohol.



  The new compound has valuable therapeutic properties.



       Example: For the mixture = 100 parts of monochloroacetone and 101 parts of phenol, 400 parts of 10.7% sodium hydroxide solution are gradually run at 20-25, with stirring. Stirring is continued, finally at <B> 50 </B> until the aqueous layer reacts neutrally.

   Then 135-145 parts of phenoxyacetone have deposited, which are lifted off, washed ge with dilute caustic, dried and distilled, bp 94-98.1. 100 parts of this are diluted with the same volume of benzene and this solution is stirred into the cold mixture of 68 parts of morpholine, 85 parts of benzene and 134 parts of formaldehyde solution at 1a within one hour. The mixture is stirred for 24 hours at room temperature, a further 3 hours at a final temperature of 45.

   After cooling, the base is extracted from the reaction mixture using dilute sulfuric acid, if necessary the acidic sulphate solution is freed by extracting any remaining neutral starting product, then concentrated and the free base is precipitated using potassium hydroxide with cooling. Traces of morpholine are removed in vacuo.

   The yield of 1-phenoxy-4-morpholinylbutanon-2 is around 78% of theory, but more than 20% phenoxyacetone is regenerated; The conversion therefore takes place, apart from the slight additional consumption of chloroacetone, almost without material loss. The product forms white crystals (from methanol), F. 97, shows the expected solubility and can be titrated as a mono-acidic base (1 g consumed against methyl orange 40.65 cm 'n! 10 acid, calculated 40.15 cm') .



  To reduce the aminoketone, dissolve it in ten to twelve times the amount of absolute alcohol, add gradually a third of the weight of the ketone to sodium to the boiling solution while passing nitrogen through it, stir the resulting suspension and gradually add another one or two Third sodium too.



  When the reduction is complete, the reaction mixture, cooled to 0, is slightly over-neutralized with ice-cold, semi-dilute hydrochloric acid, the precipitated common salt is removed and the alcohol is distilled off in vacuo. The salt paste that remains is taken up in a little water, the solution is neutralized and the isolated free base, 1-phenoxy-4-morpholinyl-butanol-2, is purified by crystallization from a lint. It comes off easily. in organic solvents and in dilute acids; is the free aminophenol alcohol. very autoxidizable, while the salts with acids are resistant to atmospheric oxygen.

 

Claims (1)

PATENT CLAIM: Process for the preparation of an ary 1 oxy-alkylamino-butanol, characterized in that phenoxyacetone is reacted with formaldehyde and morpholine to form 1-phenoxy-4- 3o morpholinylbutanone-2 and this compound is reduced to the corresponding secondary alcohol. 1-Phenoxy-4-morpholinylbutanol-2 forms white crystals which are easily soluble in organic solvents and in dilute acids. The free aminophenol alcohol is very oxidizable, while the salts with acids are resistant to atmospheric oxygen. @o The new compound has valuable therapeutic properties.