CS226933B1 - N-(2-benzoyloxyethyl)-n,n-dimethylalkylammonium bromides and method of preparing same - Google Patents

Description

The invention relates to N- (2-benzoyloxyethyl) -N, N-dimethylalkylammonium bromides of the formula

Chk (ι ΦΙ ^ύ Θ

C-O- (CH ₂ ) ₂ -NR 4 Br

CH ^ kde

R represents a linear alkyl chain having a carbon number of 8 to 16 and a process for their preparation.

Organic ammonium salts with at least one long alkyl chain are known to exhibit significant biological effects (e.g., antimicrobial, muscarinic, curareform, etc.) as well as surfactant properties and have therefore been used in practice as disinfectants, detergents, medicaments and the like. but also in organic synthesis, e.g. as interfacial catalysts or in the preparation of unsaturated compounds, in the identification of certain natural substances.

The preparation of the ammonium salts is largely based on the reaction of the respective tertiary amine with the haloalkanes under various reaction conditions, yielding the atonium salts in a variable yield. Most often the reactions are carried out in water, methanol, ethanol, nitromethane, but also in toluene and benzene.

Under these conditions, most often ammonium salts are contaminated with the decomposition products of the side reactions. The present invention utilizes the reaction of (2-dimethylaminoethyl) benzoate with 1-bromoalkanes in methyl cyanide or methanol to produce products of high purity and in very good yields.

The compounds of the present invention have been found to have unknown effects and microorganisms. In disinfectant efficacy, these substances are comparable and in some cases more effective than disinfectants of a similar type used in practice (Ajatin, Septonex).

The examples illustrate, but are not limited to, the preparation of the selected compounds, characterize them, and antimicrobial effects expressed as minimum inhibitory concentration (MIC) in µg / ml on Staphrylococcus aureus, Escherichia coli and Candida albicans are also reported.

228933

Example 1

(0.05 mol of (2-dimethylaminoethyl) benzoate dissolved in 5 ml of dry methyl cyanide is added at room temperature 0.05 mol of 1-bromidodecane and the reaction mixture is heated at 100 ° C for 8 hours. N- (2-benzoyloxy) -N, N-dimethyl-dodecylammonium bromide is recrystallized to constant melting point from dry acetone, mp 72-74 ° C;

elemental analysis (calculated ° / o / found%):

C 62.50 / 61.81, H 9.12 / 9.27, N 3.17 / 3.28; yield 92 ´% of theory;

MIC, 4, 20, 7.

Example 2

The procedure was the same as in Example 1 except that 1-bromo-tetradecane was used in the reaction and the solvent was methanol. The reaction temperature was 60 ° C, the reaction time was 16 hours. The product N- (2-benzoyloxyethyl) -N, N-dimethyltetradecylammonium bromide had m.p. t. Mp 82-84 ° C;

elemental analysis (calculated% / found%):

C 63.89 / 63.47, H 9.44 / 9.10, N 2.98 / 2.90; yield 94% of theory;

MIC: 3.70, 7.

Example 3

The procedure is identical to that of Example 1 except that 1-bromohexadecane was used in the reaction, the solvent was methyl cyanide, the temperature was 20 ° C and the reaction time was 24 hours. The product N- (2-benzoyloxyethyl) -N, N-hexadecyldimethylammonium bromide had 1.1. 88-90 ° C;

elemental analysis (calculated% / found ° / o):

C 64.86 / 65.28, H 9.70 / 9.75, N 2.81 / 2.98; yield 87% of theory;

MIC: 20, 200, 30.

All the compounds thus prepared were white crystalline, low hygroscopic substances, soluble in polar and insoluble in non-polar solvents. In addition to elemental analysis, they were also identified by spectral methods.

Claims (2)

SUBJECT We claim: 1. N- (2-Benzoyloxyethyl) -N, N-dimethylalkylammonium bromides of the general formula -CHi (Si-Si 3 C-O-ICH ^ N-R-Br CH ^ -CO? CH _{g) 2} -N-CH ₃ CH3, with 1-bromoalkane of the general formula R = Br where R is an alkyl chain of 8 to 16 carbon atoms. 2. A process for the preparation of compounds of the general formula as in 1, characterized by reacting (2-dimethylaminomethyl) benzoate of the formula: R is the same as in point 1, in a dry methyl cyanide or methanol environment at temperatures ranging from 20 to 100 ° C for 8 to 24 hours.