Purification of d,d'-2,2'(ethylenediimino)di-1-butanol dihydrochloride
AssigneeAmerican Cyanamid Company
InventorJohn Kazan
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Abstract
A superior grade of d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride from the reaction of ethylene dichloride and an excess of d-2-amino-1-butanol is obtained by mixing finely divided sodium hydroxide with the reaction mixture, vacuum distilling off d-2-amino-1-butanol, adding a 2-4 carbon alkanol, preferably isopropanol, separating sodium chloride, adding water or an aqueous 2-4 carbon alkanol thereto to a water content of about 7-10% by weight, and an essentially stoichiometric amount of hydrogen chloride, to precipitate d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride, cooling the reaction mixture, and separating a pharmaceutical grade product.
Claims4
In a process for preparing d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride comprising the steps of
- reacting excess d-2-amino-1-butanol with ethylene dichloride,
- adding to the reaction mixture thus formed sufficient finely divided sodium hydroxide to neutralize hydrogen chloride formed therein,
- distilling off unreacted d-2-amino-1-butanol, adding sufficient of a 2 to 4 carbon alkanol to the residue to dissolve the thus formed d,d'-2,2'-(ethylenediimino)di-1-butanol, separating sodium chloride therefrom,
- adding hydrogen chloride to the resulting solution to form d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride, and separating the same from said alkanol, the improvement which comprises:
- reacting a 2 carbon alkanol solution of d,d'-2,2'-(ethylenediimino)di-1-butanol with an essentially stoichiometric amount of hydrogen chloride at 40.degree.-60.degree.C. in the presence of about 7% to 10% by weight water, based on the total weight of the reaction mixture to form d,d'-2,2'-(ethylenediimino)di-1-butanol dihydrochloride,
- slowly cooling the resulting aqueous alkanol solution to 0 to -10.degree.C. to precipitate said dihydrochloride,
- separating said dihydrochloride from said aqueous alkanol solution,
- washing said dihydrochloride with a 2 to 4 carbon alkanol, and drying the same.
Dependencies are inferred from the claim text.