CS216440B1 - N, N'-bis (alkylmethyl) -1,2-ethanediamines and processes for their preparation - Google Patents

Abstract

The invention relates to N,N'-bis(alkylmethyl)-1,2-ethane-4 diamines of the general formula h 1 R -a -CHj -ch2 -n -r i L 1 where R denotes a linear alkyl chain with a number of carbon atoms of 8 to 14 and a method for their preparation from N,n'-dimethyl-1,2-ethanediamine and the corresponding 1-bromoalkanes. The compounds serve as basic raw materials for organic synthesis as well as in the preparation of biologically active and surface-active compounds.

Description

The invention relates to N, N'-bis (alkylmethyl) -1,2-ethanediamines of the general formula

R-H -CH 2 -CU 2 -N-R CH.

Where R denotes a linear alkyl chain having a number (m carbon atoms of 8 to 14 and a method for their preparation)

Compounds of this type serve as starting materials in the preparation of biologically active compounds having surface-active properties. 1 jj Lt.

So far, only 1,2-ethanediamine derivatives with all four chains of the same length are known, but only one to three carbon atoms have been used, and they have been used for the preparation of antimicrobial and surfactant compounds. The compounds of the invention are novel and have not been previously described in the chemical literature. her

It is known to prepare similar compounds starting from, for example, 1,2-dibromoethane and secondary amines or 1,2-ethanediamine and formic acid and formaldehyde, but symmetrically substituted tetraalkyl-1,2-ethanediamines are obtained. the disadvantage is that, in addition to the method using reductive alkylation, which can only be prepared by the tetramethyl derivative, the resulting products are obtained in relatively low yields and in particular non-uniform.

The process of the present invention is based on N, N'-dimethyl-1,2-ethanediamine which, by reaction with the appropriate 1-bromoalkane, yields high purity N, N'-bis (alkylmethyl) 1,2-ethanediamine. Examples include selected compounds and methods for their preparation, but the examples do not limit the scope of the method. EXAMPLE 1 0.25 mol of N, N'-dimethyl-1,2-ethanediamine was dissolved in 300 ml of dry benzene, the solution was heated to boiling and 0.5 mol of 1-bromononane was added over 1 hour. After 6 hours of reaction under reflux and cooling, the reaction mixture was filtered, the solvent was distilled off, and the residue was dissolved in 0.6 mol of concentrated hydrochloric acid. The cold solution was extracted with ether. Solid sodium hydroxide was added to the aqueous portion, the resulting amine was separated and extracted with ether. The extracts were dried over anhydrous sodium sulfate, the solvent was evaporated after filtration and the product N, N'-bis- (methylnonyl) -1,2-ethanediamine was distilled. T. v. 209 ° C / 0.04 kPa; n2 => 1.4530; Rf = 0.72 (Silufol; acetone: 1NHCl (1: 1); Dragendorf reagent detection); 41% yield. Example 2 The process as well as the batches are the same as in Example 1, instead of 1-bromononane, 1-bromotridecane was used in the reaction and the solvent was leachate. The product N, N'-bis (methyltridecyl) -1,2-ethanedcamine had a melting point of 251 ° C / 0.05 kPa; n2 '= 1.4590; R t = 0.51; yield 40% of theory. The identity of all the compounds of the invention was verified by elemental element analysis and spectral methods.

Claims (2)

PREDMET 1. N, N ' -bis (alkylmethyl) -1,2-ethanediamines of the formula R < -N > -ca-ch, -N-RII, " wherein R < 5 > denotes an alkyl chain containing from 8 to 14 carbon atoms . ·! VYNALEZU 2. A method of preparing compounds of general interest. c, as in 1, characterized in that N, N'-dimethyl-1,2-ethanediamine of the formula CH 3 - NH - CH, - CH 2 - NH - CH 3 is reacted with 1-bromoalkane containing 8-14 carbon atoms in the chain in dry benzene or toluene at the boiling point of the solvent. 216440