CS226944B1 - Tris-n-oxides of bis (2-dimethylaminoethyl)alkylamines and method of preparing same - Google Patents

Description

The present invention relates to tris-N-oxide bis (2-dimethylaminoethyl) alkylamines of the general formula

O '(CH ₃ ) ₂ N ⁺ - (CH 2) 2 - N ⁺ - (CH 2) ₃ - ⁺ N (CH ₃ ) ₂

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

It is known that some non-aromatic mono and bis amine oxides have found utility in industry due to their good surface-active properties, beneficial biological effects, low toxicity and low irritability, biodegradability as well as due to relatively simple preparation. However, the polyamine N-oxides have not been prepared.

The compounds of the invention are novel and have not yet been described in the chemical literature and have been found to have unknown biological effects. They are highly selective for gram-positive bacteria and yeast, while they do not affect gram-negative bacteria.

The process for the preparation of these compounds according to the invention consists in the oxidation of bis (2-dimethylaminoethyl) alkylamines with a 10-30% aqueous hydrogen peroxide solution at temperatures of 35 to 65 [deg.] C. After isolation, the amine oxides are produced in high yield of high purity.

In the Examples, which illustrate but do not limit the method of preparation, the method of the invention is shown and selected compounds are characterized. Antimicrobial activity expressed as minimum inhibitory concentration (MIC) in µg / ml on Staphylococcus aureus and Candida albicans strains is also shown. Compared with Ajatin (benzyldodecyldimethylammonium bromide), which is an organic ammonium salt (no N-oxide is currently used for disinfection in the CSSR), the tris-N-oxides of the present invention are most effective for both S. aureus and C. albicans Ajatin is more effective on E. coli.

Example 1

Dissolve 0.1 mol of bis (2-dimethylaminoethyl Joctylamine) in 30 ml of methanol and add 1 mol of a 10% aqueous solution of hydrogen peroxide at a temperature of 35 to 40 ° C. After 2 hours the temperature is raised to 65 ° C and After cooling, the excess hydrogen peroxide is decomposed with, for example, Pt-black, the volatiles are evaporated in a water pump vacuum, the product is freed from residual water by azeotrapic distillation with dry benzene or toluene and recrystallized to a constant melting point from acetone. 124-125 ° C; Rf ₍ acetone: 1N HCl 1: 1, Siluifol, detection by Draigendonf reagent in Munier modification) - 0.68; yield; 85% of theory; IC i _{N of} doublets 955 and 941 cm ^-1 ; MIC 800; 900.

Example 2

The procedure was the same as in Example 1 except that bis (2-dimethylaminoethyl) undecylamine and% hydrogen peroxide were used in the reaction. Form tris-N-oxide, bis- (2-dimethylaminoethyl jundecylamínu of 1.1 DZA 115 116 ° C; R _f = 0.63; 84% yield; IR in _N _O d 958-936 cm ^-1, the MIC 500, 600th

Example 3

The procedure was the same as in Example 1 except that bis (2-dimethylaminoethyl) pentadecylamine and 30% hydrogen peroxide were used in the reaction. Form tris-N-oxide, bis- (2-dimethylaminoethyl jpemtadecylamínu p, mp 112 a'ž 113 DEG C. Rf = 0.47; yield 89% of theory; IR in _N _ ₀ d 962-932 cm-l, the MIC 9; 9th

Claims (2)

SUBJECT We claim: 1. Tris-N-oxides, bis (2-dimethylaminoethyl jalkylamínov the formula (CH _{3) 2} N ⁺ - (CH 2) 2 N ⁺ (CH2) ₂ - ⁺ N (CH ₃ O} ₂ wherein R O_ R is an alkyl chain of 8 to 16 carbon atoms. 2. SpQsob a compound of formula as in 1, characterized in that the oxidized bis (2-dimetylaminoetyljalkylamin of formula (CH _{3) 2} N (0Η _{2) 2} --N- _{(CH2) 2-N} (CH ₃ ) ₂ wherein R denotes the same as in 1, a 10-30% aqueous hydrogen peroxide solution at a temperature of 35-65 ° C.