CS216438B1 - N, N'-bis (decylmethyl) -α, ω-alkanediamine dioxides and their method of preparation - Google Patents

Abstract

The invention relates to N,N'-bis(decylmethyl)-α,ω-alkanediamine dioxides of the general formula where n = 3 to 5 and 7 to 10 and a method for their preparation based on the oxidation of N,N'-bis(decylmethyl)-α,ω-alkanediamines with a 20 to 30% aqueous solution of hydrogen peroxide at temperatures of 40 to 70 °C. The final compounds have a pronounced antimicrobial effect as well as surface-active properties.

Description

(54) N, N'-bis (decylmethyl) -α, ω-alkanediamine dioxides and process for their preparation

The invention relates to N, N'-bis (decylmethyl) -a, a-alkane-dioxides of the general formula ^C 10 oot T «! L- ^<CH 2> η-Ν- <ηθ" OHj OLT 21 wherein n = 3až5a7ažl0a their methods of a preparation based on the oxidation of N, N'-bis (decylmethyl) -α, carbonandiamines with a 20 to 30% aqueous hydrogen peroxide solution at temperatures of 40 to 70 ° C.

Finally, the compounds have a pronounced antimicrobial effect as well as surface-active properties.

The invention relates to N, N'-bis (decylmethyl) -a, a-alkane-dioxides of the formula ^T-C 1O oof> 1 "* -" * 2 km ΛΛχ CA-CH, wherein n = 3až5a7ažl0a methods for their preparation.

It is known that amine oxides derived from nearopiatických amines containing at least one d (HY chain alkyl, exhibit significant antimicrobial, surfactant, and other ^{effects.! '1 1!}

To date, derivatives of similar structure are known; however, they have all alkyl chains of equal length with the number of carbon atoms in one of 1 or 2.

The compounds of the invention are novel substances which have not been previously described in the chemical literature and have been found to have unknown effects on microorganisms.

The process for the preparation of these amine oxides object of the invention is based on the oxidation of the respective tertiary diamines with an aqueous solution of 20 to 30% hydrogen peroxide.

The examples show the preparation method and characterization of selected compounds of the invention and their antimicrobial effect expressed as the minimum inhibitory concentration of MIC in pg / ml found on Staphylococcus aureus, Escherichia coli and Candida albicans. The examples do not limit the application of the .i method

Example 1,

0.1 mol of N, N'-bis (diylmethyl) -1,3-propanediamine is dissolved in methanol and 0.3 mol of a 20 to 30% aqueous hydrogen peroxide solution is slowly added at a temperature of 40 to 50 [deg.] C. The reaction is carried out for 4 hours at 60-70 ° C, after cooling: the excess hydrogen peroxide is decomposed, the water and the solvent are distilled off and the residue is dried. The crude product is recrystallized from dry acetone to a constant melting point. N, N ' -bis (decylmethyl) -1,3-propanediamine dioxide having a melting point of 125 DEG-128 DEG C. is obtained; Rf = 0.66 (Silufol; aqetopa system: 1 N HCl (1: 1), detected by Dragendroph reagent); yield 66% of theory; IR-spectral char! γ _NO 964 and 944 cm ^-1 (nujol); MIC 4Cl ·, 60 ;. after. i, '' ·

Ϊ. ^;

Example 2

The procedure was identical to that described in Example 1 except that N, N'-bis (decylmethyl) -1,5-pentanediophenyl was used in the reaction. The product is N, N'-bis (decylmethyl) -1,5-peritaridiamine dioxide monohydrate, mp 139-141 ° C; R _f = 0.63; yield 76% of theory; IR spectral characteristics γ _NO 958 and 950 cm ^-1 ; Silence 10; 30; 5. and

Example 3

The procedure was identical to that described in Example 1 except that N, N'-bis (decylmethyl) -1,10-decanediamine was used in the reaction. The product is N, N'-bis (decylmethyl) -1,10-decanediamine dioxide dihydrate mp 144-147 ° C; Rf = 0.60; yield 79%. Theory; IR spectral characteristics γ _ΝΟ 941 and 916 cm ^-1 ; MIC 50; 200; 30.

All compounds of the invention were identified by elemental analysis and spectral methods.

Claims (2)

eats with Π! OBJECT OF THE INVENTION ~ ‘'I a | . - .k. ....... - · ............. ; 1. N, N'-bis (decylmethyl) -α, ω-alkanediamine dioxides N, N'-bis (decylmethyl) -α, (ω-alkanediamines in general- of the general formula formula 0 0 t T ^C 10 * fel ^- J ^{B - t} 2 ° 10 “21— j ¹ - ⁽ “ * 2> 11 — j * ^-C io “21 CH, CM,  '1' '! i CH, CH, {'' i 1 / ' ^! where n = 3 to 5 and 7 to 10. _(t , 'and where n is the same as in 1, 20 to 30% 2. A process for the preparation of compounds of the formula I with an aqueous hydrogen peroxide solution at 40 ° C as in 1, characterized in that they oxidize to 70 ° C.