Preparation of carboxylate and sulfonate salts of 1-cis-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.13,7)decane-II

Abstract

Compounds of the .[.formulas.]. .Iadd.formula .Iaddend. ##STR1## wherein X - is a lower alkyl carboxylate .[.(I).]., a phenylcarboxylate .[.(I).]., a lower alkylsulfonate .[.(II).]. or a phenylsulfonate .[.(II).]. anion, wherein the phenyl ring may have lower alkyl, lower alkoxy, hydroxyl, amino, nitro, bromo or chloro substitution. The compounds are prepared by reacting the .[.carbinolamine.]. .Iadd.ring-opened intermediate .Iaddend.prepared by reacting cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1 3 ,7)decane chloride with aqueous sodium hydroxide, with a carboxylic or sulfonic acid, as indicated, to form the corresponding 1-cis-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1 3 ,7)decane carboxylate or sulfonate. These compounds have antimicrobial activity.

What is claimed is: 
     
       1. A compound corresponding to .[.one of.]. the .[.formulas.]. .Iadd.formula .Iaddend. ##STR6## wherein X represents a lower alkyl carboxylate, .[.(I).]. a lower alkyl sulfonate, .[.(II).]. a benzoate .[.(I).]. or a phenylsulfonate .[.(II).]. salt wherein the phenyl group may contain lower alkyl, lower alkoxy, hydroxyl, amino, nitro, chloro or bromo substitution. 
     
     
       2. The compound of claim 1 represented by formula (I) wherein X -  represents the benzoate anion. 
     
     
       3. The compound of claim 1 represented by formula .[.(II).]. .Iadd.(I) .Iaddend.wherein X -  represents the p-toluene sulfonate anion. 
     
     
       4. The compound of claim 1 represented by formula (I) wherein X -  represents the o-hydroxy benzoate anion. 
     
     
       5. The compound of claim 1 represented by formula (I) wherein X -  represents the p-hydroxybenzoate anion. 
     
     
       6. The compound of claim 1 represented by formula (I) wherein X -  represents the p-methylbenzoate anion. 
     
     
       7. The compound of claim 1 represented by formula (I) wherein X -  represents the o-aminobenzoate anion. 
     
     
       8. The compound of claim 1 represented by formula (I) wherein X -  represents the o-nitrobenzoate anion. 
     
     
       9. The compound of claim 1 represented by formula (I) wherein X -  represents the p-chlorobenzoate anion. 
     
     
       10. The compound of claim 1 represented by formula (I) wherein X -  represents the 2,4-dichlorobenzoate anion. 
     
     
       11. The compound of claim 1 represented by formula (I) wherein X -  represents the o-bromobenzoate anion. 
     
     
       12. The compound of claim 1 represented by formula (I) wherein X -  represents the acetate anion. 
     
     
       13. The compound of claim 1 represented by formula .[.(II).]. .Iadd.(I) .Iaddend.wherein X -  represents the methyl sulfonate anion. 
     
     
       14. Method for making a carboxylate or a sulfonate salt of cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1 3 ,7)decane which comprises adding to an inert, neutral organic solvent solution of .[.7 cis-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo-(3.3.1)-nonane-3-methanol.]. .Iadd.the reaction product of Dowicil-200 with excess aqueous sodium hydroxide .Iaddend.at a temperature between about 0° C. and room temperature (a) substantially two molar proportions of a lower alkyl carboxylic acid, or a benzoic acid having lower alkyl, lower alkoxy, hydroxyl, amino, nitro, chloro or bromo substitution, or (b) substantially one molar proportion of a lower alkyl sulfonic acid or a benzene sulfonic acid, respectively, in an inert, neutral organic solvent and recovering the said product from the reaction medium.