CH200183A - Process for preparing the alpha-phenyl-n-valerate of diethylaminoethanol. - Google Patents

Description

  

  Process <B> for </B> the preparation of alpha-phenyl-n-valerate of diethylarainoethanol. It has been observed by the Applicant that the esters of alpha-phenyl- acids,% liphgtiques and of amino-aliphatic-n-aliphatic-N-disubstituted alcohols possess marked spasmolytic properties, while having a particularly weak toxic action. .



  By alp-ha, -phenyl-aliphatic acids "is meant saturated or unsaturated aliphatic acids which bear a phenyl group on <B> the </B> carbon adjacent to the carboxyl group and which have the structure general re presented by the formula ,.
EMI0001.0011
    (formula in which R is a saturated or unsaturated hydrocarbon radical), that is to say 2-phenyl-propionic acid - and its higher homologues and the corresponding unsaturated compounds.



  The present invention relates to a process for the preparation of one of <I> cm esters, </I> <B> to </B> savair the alpha-phenyl-n-valerate of diethyl-a, mino-eth, auo, l, which has an int6rm-health therapeutic value, and therefore finds application in therapy.



  This process is characterized by reacting alpha-phenyl-n-valeric acid or a salt thereof with a compound yielding the remainder <B> - </B> C'H # <B> - < I> N = </I> </B> (C'll ') -.



  Here are three examples of the practical execution of this process, in which the following are reacted respectively: an alkali salt of alpha-phenyl-n-valoric acid with diethylamine chloroethane; % alpha-phenyl-n-va-leric acid with -diethylamino-chlo, rethane; and said acid with diethylaminoethanol. <I>Example</I> <B> 1:

  </B> In a <B> 500 </B> cm '<B> </B> three-callus flask, fitted with a mechanical stirrer and a reflux <B> </B> condenser, <B> 0J </B> mül-gr of potassium alpha-phenyl-n-valerate, dry and <B> 75 </B> cm 'of dry benzene are introduced, and then a solution of < B> 0.1 </B> mol-gr of CI-CH'.CH2.N (C2H5) 2 diethylaminochloroethane in <B> 50 </B> cm 'of dry benzene. The mixture is heated for 4 hours under reflux while stirring.

   The mineral salts are separated by the vage with water, and the product is then rectified by distillation. The amino ester formed:
EMI0002.0007
    end of 140 <B> 'at </B> 144 <B> C </B> under a pressure of <B> 3 </B> mm of mercury; it is a new body with attractive spasmolytic properties, while having a particularly weak toxic action. Its hydrochloride melts <B> at </B> <B> 109 0 </B> C.



  <I> Example </I> 2: Mixing <B> 0.1 </B> mol-gr of alpha-phenyl-n-valeric acid #, <B> 0.1 </B> mol- gr of diethyl-amino-chloroethane hydrochloride, <B> 0.15 </B> mol-gr of anhydrous potassium carbonate with <B> 25 </B> cm 'of acetone. The mixture is heated under a reflux condenser for <B> 10 </B> hours while stirring.

   After cooling, it is filtered, and the acetone retained in the trat wire is removed by evaporation. <B> The </B> residue is taken up in ether; the ethereal solution is washed with <B> 10% </B> sodium carbonate solution and is then extracted with <B> 5% hydrochloric acid solution. </B> This hydrochloride solution is made alkaline with sodium carbonate and is extracted with ether. After evaporation of the ether and rectification, the previously described diethylaminoethanol alpha-phenyl-n-valerate is obtained.



  <I>Example<B>3:</B> </I> Mix <B> 0.1 </B> mol-gr of alpha-phenyl-n-valeric acid, <B> 0.10 </B> mol-gr of diethylaminoethanol, <B> 80 </B> cm 'of xylene and <B> 0.13 </B> mol-gr of benzenesulfonic acid in a <B> to </ B flask > three necks, <B> 500 </B> cm ', fitted with a mechanical stirrer, a funnel and a rectification column.

   The mixture is boiled for 4 hours while adding an amount of xylene equal to <B> to </B> that which disilutes (approximately <B> 500 </B> cm 'of xylene). The xylene remaining in the flask is washed with a <B> </B> 10% sodium carbonate solution to remove the unreacted alpha -phenyl-n-valeric acid,

   then the amino ester is extracted therefrom by washing several times with <B> 5% hydrofluoric acid. </B> The amino ester released by sodium carbonate is extracted with <B> of the ether and the ethereal solution is washed with water, dried and rectified.



  As can be seen from the three examples above, it is always the same radicals of the starting bodies that are found in the finished product.

 

Claims (1)

<B> CLAIM: </B> Process for the preparation <B> of </B> the alpha-phenyl- nv & lerate of diethylaminoethanol, aerated in which the alpha-phenyl- acid is reacted n-valeric in one of its salts with a compound delivering the residue -C'H * -N <B><I>=</I> </B> (C2H5) 2. The alpha-phenyl-n-valerate of diethylaminoethanol obtained boils from 140 <B> 'to </B> 144 <B>' C </B> under a pressure of <B> 3 </B> mm of mercury, it has marked spasmolyfic properties, while having a particularly weak toxic action. SUB-SALES: <B> 1 </B> Process according to claim, characterized in that a dry benzene suspension of potassium alpha-phenyl-n-vaJérate is mixed with a dry benzene solution of diethylamino-chloroethane, in the fact that this mixture is heated, in that the mineral salts are separated therefrom and in that the ester is obtained by distillation of the final benzene solution. 2 P according to claim, characterized in that one mixes with acetone, <B> of </B> alpha-phenyl-n-valeric acid, diethylamino-chloroethane hydrochloride and an anhydrous basic substance , in that this mixture is heated and in that the ester is extracted therefrom. <B> 3 </B> A method according to claim and sub-claim 2, in that, to extract the ester, the reaction mixture is filtered after r - cold, the acetone is evaporated from the filtrate, the residue is taken up in ether, the ethereal solution is washed and neutralized from which the ester is distilled off. 4 A method according to claim, characterized in that it is mixed with, xylene, alphaphenyl-n-valeric acid, di-ethylamino # -ethanol and benzene-sulfonic acid, in <B> this </B> that this mixture is boiled, in that the reaction mixture is washed to remove the unreacted acid and in -ce that the ester is extracted therefrom .