CS229092B1 - N, N "-bis (alkyldimethyl) -3-aza-3- (p-tert-butylbenzyl) -1,5-pentanediammonium dibromides and their preparation - Google Patents

Abstract

The invention relates to N,N-bis(alkyldimethyl)-3-aza-3-(p-tert.butylbenzyl)-1,5-pentanediammonium dibromides of the general formula CH, CH, R—N—(CH2)2—N—(CH2)2—N—R 2 Brfc CHj CH2 CH, θ' ch3—c—ch3 ch3 where R denotes an alkyl chain with a number of carbon atoms of 8 to 16 or benzyl or p-tert.butylbenzyl and a method of their preparation, which consists in the reaction of bis(2-dimethylaminoethyl)-p-tert.butylbenzylamine with 1- -bromoalkene or benzyl bromide or p-tert.butylbenzyl bromide in a boiling methyl cyanide, ethanol or methanol environment for 4 hours. The final compounds exhibit antimicrobial activity against gram-positive, gram-negative bacteria and yeasts and are therefore useful as disinfectants. In addition, they also exhibit surface-active properties.

Description

229092 2

The present invention relates to N, N ' -bis (alkyldimethyl) -3-aza-3- (p-tert-butylbenzyl) -1,5-pentenediammonium dibromides of formula (3)

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

Organic mono- and bisammonium salts with at least one long alkyl chain include the cationic surfactant compounds. This property - surface activity - is also used on an industrial scale, especially for the preparation of detergents. In addition, they have found use, for example, in humane medicine (such as gangllo blocking agents and substances with a rare form of action and, last but not least, as highly effective disinfectants). They have found use in organic synthesis as interphase catalysts, where they serve both as catalysts and on the other. as the reaction medium.

The compounds of the invention have hitherto been described in the chemical literature and have not yet been known to have an effect on microorganisms. Their antimicrobial efficacy is in many cases higher than the standards of Ajatin and Septonex, currently one of the most widely used disinfectants.

There are several possible methods for preparing such type of compounds, most often using the reaction of the corresponding halogeno derivatives with tertiary amines under different reaction conditions. Since the organic ammonium salts undergo elimination reactions by heating, the extracts as well as the purity of the products under unsuitable reaction conditions are low.

The method of the invention is based on the reaction! , -bromoalkane or benzyl or 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. Products of relatively high purity are produced in good yields, which is an advantage of the method. In the examples which illustrate, but do not limit, the method of preparation, the method of the invention is described and selected compounds are characterized. Their antimicrobial activity, expressed as the minimum inhibitory concentration (MIC) in µg / ml on strains of Staphylococcus aureus, Escherichia coli and Candida albicans microorganisms, is also reported.

In Example 1, in 30 ml of methyl cyanide, 0.1 mol of bis (2-dimethylaminoethyl) -p-tert-butylbenzyl ein and 0.2 mol of 1-bromoctane are dissolved. The reaction mixture was heated to reflux for 4 hours, the solvent was distilled off in vacuo, the crude product was stripped of residual moisture, dissolved in acetone and precipitated with ether. 3-Aza-3- (p-tert-butylbenzyl) -N, N ' -bis (dimethyloctyl) -1,5-pentanediammonium dibromide is formed with mp 167-170 [deg.] C., 85% of theory;

Claims (2)

3 229092 1 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 instead of cyanogen ethanol and 1-bromododecane were used instead of 1-bromoctane. 3-Aza-3- (p-tert-butylbenzyl) -N, N ' - bis (dodecyldimethyl) -1,5-pentanediammonium dibromide is formed. 182-184 ° C; yield 86%; Hf = 0.60; MIC: 5, 30, 5. EXAMPLE 3 The working procedure is the same as in Example 1 except that 1-bromohexadecane was used in place of 1-bromoctane and methanol was the solvent. 3-aza-3 - (p-tert-butylbenzyl-D-β-bis (hexadecyldimethyl) -1,5-pentanediammonium dibromide is formed with mp 164-167 ° C, 89% yield; Kf = 0.44; MIC : 50, 400, 200. EXAMPLE 4 The procedure is the same as in Example 1 except that p-tert-butylbenzylbroraide was used in place of 1-bromoctane in the reaction, resulting in 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. OF THE INVENTION 1. N, N "-bis (alkyldimethyl) -3-aza-3- (p-tert-butylbenzyl) -1,5-pentanediammonium dibromide general formula wherein R represents an alkyl chain having from 8 to 16 carbon atoms or benzyl, respectively; p-tert-butylbenzyl. 2. A process for the preparation of compounds of formula (1), characterized in that bis (2-dimethylaminoethyl) -p-tert-butylbenzylamine with 1-bromoalkane containing from 8 to 16 carbon atoms in the chain or benzyl or benzyl, respectively, is not reacted. p-tert-butylbenzyl bromide in methyl ethyl amide, ethanol or methanol at the boiling point of the solvent for 4 hours.