CS240389B1 - N- [2- (dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides and their preparation - Google Patents

Abstract

The invention relates to N-[2-(dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides of the general formula O CH3 CuHSs—C—N—CH2—CH2—N+—R BrCH3 CH3 where R denotes a linear alkyl chain with the number of carbon atoms from 2 to 14 and the method of preparation of these compounds, which consists in the reaction of the respective 1-bromoalkane with N,N',N'- -trimethylaminoethylamide of dodecanoic acid in methyl cyanide at the boiling temperature of the solvent. Finally, the compounds have significant surface-active properties and antimicrobial effects on gram-positive and gram-negative bacteria as well as yeast. The most effective of them can be used as disinfectants with a detergent effect in cosmetics, pharmaceuticals, etc. wherever it is possible to use their properties of surfactants or antimicrobial active substances, or in a combination of both these properties.

Description

240389

The invention relates to N- [2- (dodecanoylmethyl-amino) ethyl] alkyldimethylammonium bromide of general formula O CH3

C11H23-C-N-CH2-CH2-N + -R Br "CH3 CH3 wherein R is a linear alkyl chain having from 2 to 14 carbon atoms and the preparation of these compounds.

Long chain aliphatic carboxylic acids and their derivatives represent compounds which, besides their great biological importance, have industrial uses. Due to their excellent surfactant properties and negligible side effects, they are advantageously used, in particular hydroxyalkyl amides with secondary amide groups, in cosmetics, farms and in various industries. Of this type of compounds, do-decanoic acid derivatives are most widely used, but compounds with a short or longer alkyl chain are also known. This hydrocarbon chain may be saturated or unsaturated, optionally substituted.

Ammonium salts of omega-aminoalkylamides of carboxylic acids having a substituted omega-amino group which are used in the form of beta-amines or ammonium chlorides are less known and used. Tertiary amide derivatives (except bis [hydroxyethyl] compounds) are only used to a very limited extent.

The compounds of the invention which contain a tertiary amide group in their molecule and 2 to 14 carbon atoms per ammonium nitrogen-bound alkyl chain have not been known to date. Until now, Zistilisa has not been known to have effects on microorganisms, the most effective of which is to have a higher effect than the commonly used organic ammonium disinfection agents - Ajatin and Septonex. Also, all of these compounds were found to have unknown surface active properties. Compared with compounds of a similar type containing its molecule, a secondary amide group, these compounds are more preferred in view of the fact that, due to the presence of a tertiary amide group, the possibility of the formation of N-nitrosamines (found in secondary amides) by the compounds by the compounds is excluded. significant carcinogenic effect.

The process for the preparation of the compounds of the present invention is carried out in the reaction of N, N,, N‘-trimethylamino-dodecanoic acid amide with the corresponding 1-bromoalkane in methyl cyanide to boil the solvent. The method of the invention has the advantage over other methods of preparing organic ammonium salts (e.g., water, methanol, ethanol, and reaction medium) that by-products (e.g., hydrolytic or pre-esterification) are avoided. reactions) and the resulting compounds are formed in high yields and high purity. The examples illustrate a method for preparing selected compounds of the invention. In addition to yield, melting point, RF-values (determined by silica gel in acetone: 1 M HCl 1: 1, Dragendorf reagent in Mueller modification), IC-spectral characteristics (measured in nujol suspension, v cm-1), their critical concentration of Ck (mole dm < 3 > m) micelle formation, maximum reduction in the surface tension of Ck (yck, in ffNN ' 1), as well as antimicrobial activity against Staphylococcus aureus , Escherichia coli and Candida albicans expressed as the minimal inhibitory concentration of MICv, g. cm'3. EXAMPLE 1 0.1 mol of dodecanoic acid N, N, N, N-trimethylaminoethylamide are dissolved in 30 cm @ 3 of cyanide, 0.11 mol of 1-bromoethane is added and heated at the boiling point of the solvent. After evaporation of the solvent, it crystallizes to a constant melting point. N- [2- (dodecanoylmethylamino) ethyl] ethyl-dimethylammonium bromide is obtained in a yield of 99%; mp 74-75 ° C;

Rf = 0.52; IR: v Ne 2 2725, ω c = o 1640, δ (CH 2 N.CJrocking 1187, 1,019, p ch 2 716;

Ck = 9.1. Yck = 43.2; MIC: 50, 200, 80. Ex

The working procedure is the same as in Example 1 except that 1-bromooctane was used instead of 1-bromoethane in the reaction. N- [2- (dodecanoylmethylamino) ethyl] octyldimethylammonium bromide was obtained in 85% yield; mp 76-78 ° C; RF = 0.70; IR: NCH3 2728, v c = 1 640,

Claims (2)

SUBJECT 1. N- [dodecanoylmethylamino) ethyl] alkyldimethylammonium bromides of the general formula O CH3 II I C11H23 — C — N — CH2 — CH2 — N ⁺ —R Br- CH 3 CH 3 wherein R represents an alkyl chain having 2 to 14 carbon atoms. 2. A process for the preparation of compounds of the general formula as in 1, which comprises reacting dodecanoic acid N, N @ -, N @ - trimethylaminoethylamide of the formula: t. t. 88-90 ° C; - _Rf = 0.63; IR: NCH3 2,727, c-o 1,634, S (CH 3 N, C) rocking 1193, 1016, p ch2 721; C _k = 1.3. ⁴ '⁴; _{rc k} = 27.5; MIC: 500, > 1,000, 80. INVENTION ABOUT CnHa3-C-N-CH2-CH-N (CH 3) 2 CH3 with 1-bromoalkane of the general formula R = Br wherein R is as defined in point 1, in methyl cyanide at the solvent temperature.