CS229092B1 - N,n'-bis/alkyldimethyl/-3-aza-3-/p-tert.butyl-benzyl/-1,5-pentanediammonium dibromides and method of preparing same - Google Patents

Abstract

The invention relates to N, N-bis (alkyldimethyl) - 3-aza-3- (p-tert-butylbenzyl) -1,5-pentándiamoniumďibromidov formula CH, CH, R — N - (CH 2) 2 —N— (CH 2) 2 —N — R 2 Brfc CH 2 CH 2 CH, θ ' CH3-C-CH3 CH3 wherein R represents an alkyl chain of carbon atoms of 8 to 16 or benzyl or p-tert-butylbenzyl and the method for their preparation, which consists of reacting bis (2-dimethylaminoethyl) -p-tert-butylbenzylamine with 1- -bromoalkene or benzyl bromide; \ tor. \ t p-tert-butylbenzyl bromide in the medium boiling methylene cyanide, ethanol or methanol for 4 hours. Finally, the compounds exhibit antimicrobial activity effectiveness on gram-positive, gram-negative bacteria and yeast and are therefore useful as disinfectants. In addition, they report and surface-active properties.

Description

The invention relates to N, N-bis (alkyldimethyl) -3-aza-3- (p-tert-butylbenzyl) -1,5-pentanediammonium dibromides of the general formula ₃

wherein R represents an alkyl chain of 8 to 16 carbon atoms or benzyl, respectively. p-tert-butylbenzyl and a process for their preparation.

Organic mono- and bisammonium salts with at least one long alkyl chain belong to the group of cationic surfactants. This property - surface activity - is also used on an industrial scale, especially for the preparation of detergents. Moreover, they have found use, e.g. also in human medicine (as ganglioblocking agents and curareforming agents and last but not least as high-efficiency disinfectants). They have also found application in organic synthesis as interfacial catalysts, where they serve both as a catalyst itself and as a reaction medium.

The compounds of the invention have not yet been described in the chemical literature and have been found to have unknown effects on microorganisms. Their antimicrobial efficacy is in many cases higher than the standards of Ayatin and Septonex, currently one of the most widely used disinfectants.

There are several possible methods for preparing this type of compounds, but most often the reaction of the corresponding halogen derivatives with tertiary amines is used under various reaction conditions. Since organic ammonium salts are subject to elimination reactions by heating, the yields and purity of the products are poor under the chosen reaction conditions.

The method of preparation according to the invention is based on the reaction! 1-bromoalkane or benzyl, respectively; p-tert-butylbenzyl bromide with bis (2-dimethylaminoethyl) -p-tert-butylbenzylamine in methyl cyanide, ethanol or methanol at the boiling point of the solvent for 4 hours. The products of relatively high purity are obtained in good yields, which is an advantage of the method mentioned.

In the examples, which illustrate but do not limit the preparation method, the method of the invention is shown and selected compounds are characterized. Their antimicrobial activity expressed as minimum inhibitory concentration (MIC) in µg / ml on Staphylococcus aureus, Escherichia coli and Candida albicans strains is also reported.

Example a d 1

Bis (2-dimethylaminoethyl) -p-tert-butylbenzyleinine (0.1 mol) and 1-bromooctane (0.2 mol) were dissolved in methyl cyanide (30 ml). The reaction mixture was heated under reflux for 4 hours, the solvent was distilled off in vacuo, the crude product was freed of residual moisture, dissolved in acetone and precipitated with ether. There was thus obtained 3-aza-3- (p-tert-butylbenzyl) -N, N-bis (dimethyloctyl) -1,5-pentanediammonium dibromide, mp 167-170 ° C; yield 85% of theory; Rf ₍ acetone system;

N HCl 1: 1, Silufol, detection by Dragendorf reagent in Munier modification) = 0.76; MIC: 50, 500, 200.

Example 2

The procedure is the same as in Example 1 except that ethanol is used instead of methyl cyanide and 1-bromododecane is used instead of 1-bromooctane. There was thus obtained 3-aza-3- (p-tert-butylbenzyl) -N, N'-bis (dodecyldimethyl) -1,5-pentanediammonium dibromide, mp 182-184 ° C; yield 86%; _Rf = 0.60; MIC: 5, 30, 5.

Example 3

The operating procedure is the same as in Example 1 except that 1-bromo-hexadecane was used in the reaction instead of 1-bromooctane and the solvent was methanol. There was thus obtained 3-aza-3- (p-tert-butylbenzyl-4 ', 4' - bis (hexadecyldimethyl) -1,5-pentanediammonium dibromide, mp 164-167 ° C, yield 89%; R _f = 0.44; MIC: 50, 400, 200.

Example 4

The procedure was the same as in Example 1 except that p-tert-butylbenzyl bromide was used in the reaction instead of 1-bromooctane. There was thus obtained 3-aza-N, N'-bisdimethyl-3-N, N'-tris (p-tert-butylbenzyl) -1,5-pentanediammonium dibromide as an oily product; yield 88%; _Rf = 0.80; MIC: 70, 500, 300.

Claims (2)

OBJECT OF THE INVENTION 1. N, N-bis (alkyldimethyl) -3-aza-3- (p-tert-butylbenzyl) -1,5-pentanediammonium dibromides of the general formula wherein R represents an alkyl chain having a carbon number of 8 to 16 or benzyl, respectively. p-tert-butylbenzyl. 2. A process for the preparation of compounds of formula (I) as defined in claim 1, which comprises reacting bis (2-dimethylaminoethyl) -p-tert-butylbenzylamine with 1-bromoalkane having from 8 to 16 carbon atoms in the chain or benzyl, respectively. p-tert-butylbenzyl bromide in methyl amide, ethanol or methanol at the boiling point of the solvent for 4 hours.