DE187209C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- JV! 187209 - CLASS \ 2q. GROUP

Process for the preparation of benzoylalkylamino alcohols.

Patented in the German Empire on February 10, 1906.

It has been found that the benzoic acid esters of the alkylamino alcohols by their anesthetic abilities are therapeutically valuable can be demonstrated by Benzoic acid ester heated with an alkamine. Both alkyl and aryl esters can be used Find.

Example I.

3 parts of methyl benzoate and 7 parts of diethylaminoethanol are heated to boiling in an oil bath for 10 to 20 hours; the excess diethylaminoethanol and approximately unchanged methyl benzoate are then distilled off in vacuo. The remaining reaction product is dissolved in ether and the resulting alkamine ester is removed from this solution by means of dilute hydrochloric acid. After supersaturation with alkali, the diethylaminoethahol ester is taken up with the ether, dried and the base remaining after evaporation of the ether is distilled in vacuo in order to obtain the benzoic acid diethylaminoethanol ester in pure form. It forms a colorless oil that ^{distills at 132 0} and 5 mm pressure. The chlorine hydrate, represented by neutralizing the benzoyl diethylaminoethanol with alcoholic hydrochloric acid and evaporating the alcohol, remains as a crystal mass. By recrystallization from ether alcohol obtained it in beautiful needles melting at 124 ^0, which readily dissolve in water and alcohol.

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Example II.

Part of phenyl benzoate and 2 parts of dimethylaminoethanol are heated to 170 to 180 ° for 10 to 12 hours. Unchanged dimethylaminoethanol and the split off phenol are then distilled off in vacuo. The residue is dissolved in ether and the ethereal solution extracted with dilute hydrochloric acid. The benzoyldimethylaminoethanol is separated from the hydrochloric acid solution obtained using potassium carbonate and taken up with ether. After small amounts of phenol have been removed by washing with dilute sodium hydroxide solution, the ethereal solution is dried with potash and, after the ether has been distilled off, the benzoyldimethylaminoethanol is obtained as a non-crystallizing oil. It can be cleaned by distillation in vacuo. Its hydrochloride is very easily soluble in water and alcohol. From acetone, it crystallizes in beautiful, shiny needles that melt ^{at 148 0.}

Example III.

iooTeileBenzoesäureäthylesterund2OO Diamylaminoäthanol parts are heated for about 12 hours under a reflux condenser to 190 ^0th About 15 parts of the mixture are then distilled off in vacuo in order to remove the ethyl alcohol which has been split off. The residue is heated again to 12 hours on 190 ^0th Then

Claims (1)

the split off ethyl alcohol and unchanged benzoic acid ethyl ester is in vacuo and diamylaminoethanol distilled off as possible. The distillation residue is dissolved in ether and the resulting shake is shaken Benzoesäurediamylaminoäthanolester with dilute hydrochloric acid. The hydrochloric acid obtained Solution is supersaturated with ammonia and the deposited alkamine ester with ether ίο added. After distilling off the In ether, the ester is obtained as a thick, non-crystallizing oil. Can be used for cleaning convert the benzoyldiamylaminoethanol into the poorly soluble, acidic oxalate. The latter strongly crystallized from diluted alcohol in fine needles, melting at 158 ^0th The chlorine hydrate crystallizes from vinegar-ligroin in fine needles with a melting point The salt is easily soluble in water, alcohol, acetone and vinegar ether. Example IV.
100 parts of diethylaminopropanol CH ₃ CH (OH) CH ₂ N (C ₂ HJ ₂
and 50 parts of methyl benzoate are heated 12 hours 170 ^0th Then distilled in vacuo unchanged Diäthylaminopropanol and methyl benzoate, and heated again 12 hours the distillate 170 ^0th After again distilling off in vacuo, the distillation residue is taken up in ether and the alkamine ester is removed from the ethereal solution by shaking out with dilute hydrochloric acid. The hydrochloric acid solution is supersaturated with soda and the oily base which has deposited is dissolved in ether. After washing with water, drying with potassium carbonate and distilling off the ether, the benzoyl diethylaminopropanol remains as an oil that does not crystallize. Its chlorohydrate forms dissolvable crystals that are very easily soluble in water, alcohol, acetone and vinegar ether. The oxalate is also a very easily soluble salt. The picrate crystallizes from dilute alcohol in beautiful yellow skewers and melts at 146 ⁰ . Pate ν T-A ν SPRU c η: A process for the preparation of benzoylalkylamino alcohols, consisting in that non-basic esters of benzoic acid are heated with alkylamino alcohols.