CS257372B1 - N-oxides of 1-alkoxy-2-dimethylaminoethanes and processes for their preparation - Google Patents

Abstract

The purpose of the N-oxides of 1-Alkoxy-2-dimethylaminoethanes is to improve the water solubility and antimicrobial properties of 1-Alkoxy-2-dimethylaminoethanes. The stated purpose is achieved by using N-oxides-1-alkoxy-2-dimethylaminoethanes of the general formula I where R represents heptyl, octyl, nonyl, decyl, undecyl, or dodecyl and the method of their preparation in such a way that the l-alkoxy-2-dimethylaminoethanes of the general formula II R—OCH2CH2—N— (CH2)3 (II), where R represents heptyl, octyl, nonyl, dodecyl, undecyl, or dodecyl, oxidize 25 to 30 °/o wt. with an aqueous solution of hydrogen peroxide at a temperature of 50 to 60 °C. N-Oxides of 1-Alkoxy-2-dimethylaminoethanes are used in the chemistry of surfactants and disinfectants.

Description

257372

The invention relates to N-oxides of 1-alkoxy-2-dimethylaminoethanes and to their preparation. 1-Alkoxy-2-dimethylaminoethanes are known antimicrobial compounds for years. It is prepared by the condensation of sodium alcoholate with N-dimethylaminoethyl chloride, or by reaction of sodium N-dimethylamino-ethanolate with an alkyl bromide, or alkyl iodide [G. F. Grail, L.E. Tenenbaum, A.V. Tolstouchov: J. Amer. Chem. Soc. 1313 (1952); . T. Clarke, J. Chem. Soc. 1808 (1912); L. Binet, D. Kohler: Compt. rend.soc. biol. 345 (1941)). However, the practical use of the antimicrobial properties of these compounds is prevented by their poor solubility in the water. They were not able to dissolve them even with different detergents. The water-soluble salts of these compounds, however, are not compatible with conventional anionic surfactants and detergents because they form cationic surfactants.

These disadvantages are eliminated by the present invention. SUMMARY OF THE INVENTION The present invention relates to N-oxides of 1-alkoxy-2-dimethylaminoethanes of the formula I R- OCH2CH5N- (CH2 2 * 4 O (I))

wherein R is heptyl, octyl, nonyl, decyl, undecyl, or dodecyl. The invention furthermore relates to a process for the preparation of a compound of formula I, wherein the compound is: 1-alkoxy-2-dimethylaminoethane of formula II R-OCH 2 CH 2 -N (CH 2) 3 (II) wherein R is heptyl, octyl, nonyl, decyl, undecyl, or dodecyl, is treated with 30 wt. with an aqueous solution of hydrogen peroxide at a temperature of 50 to 60 ° C. The advantage of N-oxides of 1-alkoxy-2-dimethylaminethane over 1-alkoxy-2-dimethylaminoethane and their hydrochloride is good water solubility, antimicrobial efficacy and stability in aqueous solutions or dry state. Another advantage of 1-alkoxy-2-dimethylaminoethanes N-oxides is their compatibility with conventional anionic surfactants. EXAMPLE 1 18.7 g (0.1 mol) of 1-heptyloxy-2-dimethylaminoethane were dissolved in 30 ml of 96% strength ethanol and 30 ml of 30% by weight were added dropwise to the solution. aqueous hydrogen peroxide solution for 30 minutes. The temperature is maintained at 50-60 ° C during the dropwise addition and then for 4 hours. Adding the entire amount of hydrogen peroxide to the reaction mixture becomes cloudy, but clarifies during heating because the N-oxide formed is more soluble in the water / alcohol mixture. After cooling, 0.1 g of pdO2 is added to the mixture and left to stand for 2 days until the excess hydrogen peroxide is decomposed. The oxide platelet is filtered off and water with ethanol is distilled off from the filtrate at a pressure of 3 kPa. The N-oxide is then dried in a desiccator over phosphorus pentoxide. The yield was 94%, i.e. 19.1 g of N-1-heptyloxy-2-dimethylaminethane oxide. These determining absorption bands hurt in the infrared spectrum: 2,955, 2,920, 2,850.2 760, 1,462, 966 and 720 cm -1. In the mass spectrum, the following peaks were: 187,173, 102, 88 and 72.

Elemental analysis for C 11 H 25 NO 2, MW 203.3 Calculated: 64.93% by weight. % carbon, 12.30 wt. % hydrogen, 6.89 wt. nitrogen found: 64.78 wt. % carbon, 12.41 wt. % hydrogen, 6.79 wt. nitrogen. N-oxide 1-heptyloxy-2-dimethylaminoethanum bacteriostatic activity on species of Staphylococcus aureus, Staphylococcus epidermidis and Bacillus sub-tilis 100 mg microorganisms. I '1. Example 2

The procedure is as in Example 1, except that 20.1 g (0.1 mol) of 1-octyloxy-2-dimethylaminoethane are used in place of 1-heptyloxy-2-dimethylaminoethane. 95%, i.e. 20.6 g of 1-octyloxy-2-dimethylaminoethane N-oxide. The teratostatic and functional activity on Staphylococcus aureus and Staphylococcus e-pidermidis is 10 mg. I-1, Bacillus subtilis, Streptococcus faecalis and Canidida albicans are effective concentrations of 100mg. if. Example 3

The procedure is as in Example 1 except that 21.5 g (0.1 mol) of 1-nonyloxy-2-dimethylaminethane are used in place of 1-heptyloxy-2-dimethylaminoethane. Yield 90%, i.e. 20.8 g of 1-nonyloxy-2-dimethylaminoethane N-oxide. The bacteriostatic and fungistatic activity of the species Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis and Streptococcusfaecalis is 10 mg. I-1, Trychophyton ter-rest and Candida albicans is an effective concentration of 100 mg. I-1.

Claims (2)

SUBJECT CLAIMS 1. N-oxides of 1-alkoxy-2-dimethylaminoethanes of the general formula I wherein Al is wherein R is heptyl, octyl, nonyl, decyl, undecyl, or dodecyl. 2. A process for the preparation of the N-oxides of 1-alkoxy-2-dimethylaminoethanes of the formula I according to claim 1, characterized in that 1-alkoxy-2-dimethylaminoethanes of the formula II R-OCH2 CH2-N- (CH2) 3 (II) wherein R is heptyl, octyl, nonyl, decyl, undecyl, or dodecyl are oxidized by 25 to 30 wt. aqueous hydrogen peroxide solution in ethanol at 50-60 ° C.