CH278409A - Process for the preparation of a new local anesthetic. - Google Patents

Description

  

  Process for the preparation of a new local anesthetic. The use of alkyloxybenzoic acid derivatives as local anesthetics has been described several times in the literature and in patents [C. Rohmann and B. Scheurle, Arch. Pharm. 274, 110, 126 (1936); J. St. Pierce et al., J. Am. Söc. 64, 1691, 2884 (1942); USP 1193650; DRP. 522064; DRP 658389; USP 2439818; USP 2448996].

   These are always mono- or dialkylaminoalkyl esters of mono- or dialkyloxybenzoic acids, which in the core can also be otherwise substituted. In contrast, basic substituted alkylamides have only become known to date from heterocyclic carboxylic acids with alkoxylated nucleus [K. Miescher, Helv. 15, 163 (1932); J. Büchi, P.

   Lobhart and L. Ragaz, Helv. 30, 507 (1947)].



  It has been found that mono- or dialkylaminoalkylamides of alkyloxybenzoic acids in which the two alkyl radicals with the nitrogen atom of the amino group are also a heterocyclic radical, eg. B. a pyrrolidyl or piperidyl radical, and which can be prepared in a manner known per se, are effective local anesthetics.

    Those compounds of this series in which the alkyloxy group is in the m position to the carbonamide group and has more than two carbon atoms are particularly valuable. Compounds of this type show an unusually long-lasting effect and are useful for both surface and line anesthesia.

      The subject of the present patent is a process for the preparation of 3-n-butyloxy-benzoic acid-4'-diethylamino-1'-methy 1-1'-butylamide, which is characterized in that a compound which is capable is to give the 3-n-butyloxy-benzoyl residue, with 4-diethylamino-1'-methyl-1'-aminobutane.

           Example: To a solution of 47.4 g of 4-diethylamino-l-methy 1-1-amino-butane in 300 cm3 of a dry mixture of 3.5 parts of benzene and 1.3 parts of methylene chloride is added dropwise with stirring and Ice cooling at an internal temperature of 35 to 40 a solution of 63.6 g of 3-n-butyloxy-benzoyl chloride in 64 cm3 of the solvent mixture mentioned and stirred for one hour without cooling.

   Then it is shaken out twice with 10% soda solution, dried with potash and the solvents removed, finally in a vacuum. The residue is dissolved in so much, about 1N hydrochloric acid, that the solution obtained is Congo acidic. After washing twice with ether, make alkaline with soda solution and take up the precipitated base in benzene. After drying with potash and chasing the solvent, the residue is distilled in vacuo.

   The 3-n-butyloxybenzoic acid-4'-diethylamino-1'-methyl-1'-butylamide is obtained as a yellowish oil with a boiling point of 184 to 188.

 

Claims (1)

PATENT CLAIM: Process for the production of a new local anesthetic, characterized in that a compound which is capable of releasing the 3-n-butyloxy-benzoyl radical is reacted with 4'-diethy lamino-1'-methyl-1'-aminobutane . The new connection is a yellowish l51 with a bp 0.01 184 to 188 <B> 0 </B>.