CS216441B1

CS216441B1 - N-alkyl-N, N'-dimethyl-1,2-ethanediamines and a process for their preparation

Info

Publication number: CS216441B1
Application number: CS106281A
Authority: CS
Inventors: Ferdinand Devinsky; Ivan Lacko; Ludovit Krasnec
Original assignee: Ferdinand Devinsky; Ivan Lacko; Ludovit Krasnec
Priority date: 1981-02-16
Filing date: 1981-02-16
Publication date: 1982-10-29

Abstract

yynález sa týká N-alkyl-N,N'-dimetyl-1,2-etándiatnínov všeobecného vzorca kde R značí alkylový reťazec s počtom atómov uhlika 8 až 14 a spósobu přípravy týchto zlúčenín,. ktorý spočívá v reakcii N,N'-dimetyl-1,2-etándiamínu s 1-brómalkánom v prostředísuchého benzénu alebo toluénu pri teplote varu rozpúšťadla. Finálně produkty slúžia ako východiskové látky přej oijganickú syntézu, pre přípravu biologicky účinných zlúčenín s povrchovoaktívnymi vlastnosťami.The invention relates to N-alkyl-N,N'-dimethyl-1,2-ethanediatins of the general formula where R denotes an alkyl chain with the number of carbon atoms from 8 to 14 and the method of preparation of these compounds. which consists in the reaction of N,N'-dimethyl-1,2-ethanediamine with 1-bromoalkane in dry benzene or toluene at the boiling temperature of the solvent. Finally, the products serve as starting materials for organic synthesis, for the preparation of biologically effective compounds with surface-active properties.

Description

Vynález sa týká N-aIkyl-N,N'-dimetyl-l,2-etándiamínov všeobecného vzorca R—M- CH2~ CH2-NH—CHj CHj kde R značí lineámy alkylový reťazec s počtom atómov uhlíka 8 až 14.The present invention relates to N-alkyl-N, N'-dimethyl-1,2-ethanediamines of the formula R-M-CH 2 -CH 2 -NH-CH 2 CH 3 wherein R is a linear alkyl chain having from 8 to 14 carbon atoms.

Pri príprave niektorých derivátov 1,2-etándiamínu, ktoré majú biologické, detergenčné a povrchovoaktívne vlastnosti je výhodné vychádzať z trisubstituovaného diamínu vyššie uvedeného vzorca, pretože je možné na dusík viazať rózne substituenty ovplyvňujúce vyššie uvedené vlastnosti, pričom sa získajú nesymetricky substituované terciárně aminy, ktorých příprava iným spósobom je obtiažna.In the preparation of certain 1,2-ethanediamine derivatives having biological, detergent and surfactant properties, it is preferred to start from the trisubstituted diamine of the above formula, since various substituents affecting the above properties can be bonded to the nitrogen to give unsymmetrically substituted tertiary amines of which preparation in another way is difficult.

Zlúčeniny, ktoré sú predmetom vynálezu, sú nové v chemickej literatúre doteraz neopísané. Spósob přípravy, którý je predmetom vynálezu, vychádza z reakcie N,N'-dimetyl-l,2-etándiamínu s příslušným 1-brómalkánom v prostředí suchého benzénu alebo toluénu pri teplote varu rozpúšťadla. V príkladoch je uvedená metoda přípravy vybraných zlúčenín, ktoré sú predmetom vynálezu a ich charakterizácia. Příklady v žiadnom případe neobmedzujú rozsah použitia tejto metody.The compounds of the invention are not yet described in the chemical literature. The process of the invention is based on the reaction of N, N'-dimethyl-1,2-ethanediamine with the corresponding 1-bromoalkane in dry benzene or toluene at the boiling point of the solvent. In the examples, a method for preparing selected compounds of the invention and their characterization is provided. The examples do not in any way limit the scope of application of this method.

Claims

SUBJECT 1. N-alkyl-N, N'-dimethyl-1,2-ethanediamines of the general formula r-N-ca2-c2-NH-CH3 CH3 wherein R is an alkyl chain of 8 to 14. Example 1 0.25 moles of N, N'-dimethyl-1,2-ethanediamine are dissolved in dry benzene and heated to boiling. 0.25 mol of 1-bromononane is slowly added to the solution at this temperature for 1 hour. After all the alkylating agent was added, the reaction mixture was heated under reflux for 6 hours. After cooling, the mixture was filtered, and benzene was distilled off from the filtrate. The residue is purified by treatment with concentrated hydrochloric acid and liberation of the amine from its ammonium salt by treatment with NaOH. After extraction with ether, drying the extracts with anhydrous Na 2 SO 4 and distilling off the solvent, the product which is N-nonyl-N, N'-dimethyl-1,2-ethanediamine is distilled. Mp 141 ° C / 1.6 kPa; n 2 / t = 1.4459; R f = 0.79 (Silufol; acetone: 1 N HCl (1: 1); detection by Dragendorf reagent); yield 43% of theory. Example 2 The process as well as the batches are the same as in Example 1, using 1-bromotridecane and, as solvent, dry toluene. The product N-tridecyl-N, N'-dimethyl-1,2-ethanediamine had a melting point of 196 ° C / 2.1 kPa; n2 ?, = 1.4508; Rf = 0.64; yield 42% of theory. All compounds of the invention were identified by elemental elemental analysis and spectral methods. THE INVENTION

2. A process for the preparation of compounds of formula (1), characterized in that N, N'-dimethyl-1,2-ethanediamine is reacted with 1-bromoalkane containing 1-bromoalkane in the chain. 8 to 14 carbon atoms in boiling benzene or toluene. 216441