CS216899B1 - N-alkyl-n,n-dimethyl-1,2-propandiamines and method of preparation thereof - Google Patents

Abstract

The invention relates to N-alkyl-N, N'-dlmethyl-1, 2-propanediamines of the general formula R-N-CH2-CH-NH-CH3 CH3 CH3 wherein R is an atomic chain carbon 14 to 14 and the method of preparation of these compounds, which consists in the reaction of N, N'-dimethyl-1,2-propanediamine with the corresponding 1-bromoalkanes in a boiling non-polar environment solvent. Finally, the products serve as a starting point substances for organic synthesis, for preparation biologically active compounds with a surface active qualities.

Description

The present invention relates to N-alkyl-N, N'-dimethyl-1,2-propanediamines of the general formula

R-N-CH, -CH-NH-CH ₃ CH ₃ CH ₃ wherein R is an alkyl chain having a carbon number 8 to 14 and methods of preparing such compounds.

In the preparation of some unsymmetrically substituted 1,2-propanediamine derivatives, it is preferable to start from the compounds of the above formula, since another nitrogen-bound substance may be of a different nature, which in turn affects the properties of the compounds thus prepared, whether biological or physicochemical.

To date, only derivatives of a similar type derived from 1,2-ethanediamine and 1,3-propanediamine are known whose alkyl chain R contains no more than 3 carbon atoms.

The compounds of the invention are novel, not yet described in the chemical literature. They serve as starting compounds in organic syntheses and as intermediates in the preparation of biologically active substances, in particular with antimicrobial action, and as raw materials in the preparation of surface-active compounds. The process according to the invention is based on the object of reacting N, N'-dimethyl-1,2-propanediamine with the corresponding 1-bromoalkane in boiling benzene or toluene.

The examples illustrate the preparation process as well as the characterization of selected compounds of the invention. Their identity was verified by elemental analysis, ΉNMR and IR spectroscopy. The examples do not limit the application of the method.

Example 1

Dissolve 0.25 mol of N, N'-dimethyl-1,2-propanediamine in dry benzene, heat to boiling and slowly add 0.25 mol of 1-bromononane over 1 hour. After heating under reflux for 6 hours and cooled, benzene was distilled off, ether was added to the residue and the precipitated salt was filtered off. The amine is freed by treatment with NaOH, extracted with ether, dried over anhydrous Na ₂ SO ₄ and distilling off the ether amine distilled. There is a N-nonyl-N, N-dimethyl-l, 2-propanediamine with telephone 183 DEG -185 DEG C. at 1.8 psi, n = ^2% l, 4448, _Rf = 0.73 (Silufol, acetone system: 1 N HCl (1: 1), detection by Dragendorf reagent); yield 34% of theory.

Example 2

The procedure is the same as in Example 1, 1-bromo-tetradecane was used in the reaction and the solvent was dry toluene. Ntetradecyl-N, N'-dimethyl-1,2-propanediamine has a mp of 180-182 ° C / 0.16 kPa; n ²⁰ D = 1.4480; _Rf = 0.56; yield 31% of theory.

Claims (2)

N-alkyl-N, N'-dimethyl-1,2-propanediamines of the general formula R-N-CH, -CH-NH-CH ₃ CH ₃ CH ₃ wherein R is an alkyl chain having a carbon number 8 to 14. 2. A process for the preparation of compounds of the general formula as in 1, characterized by reacting N, N'-dimethyl-1,2-propanediamine of the formula CH ₃ CH ₃ —NH — CH ₂ —CH — NH — CH ₃ with 1-bromoalkane having 8 to 14 carbon atoms in a boiling benzene or toluene environment.