CS216439B1 - N, N'-bis (alkylmethyl) -1,2-propanediamines and a method for their preparation - Google Patents

Abstract

The invention relates to N,N'-bisalkylmethyl-1,2-propanediamines of the general formula: R-M-O-C-R-CH-CH-CH, where R is an alkyl chain with 8 to 14 carbon atoms, as well as to a method for preparing these compounds from N,N'-dimethyl-1,2-propanediamine and the corresponding 1-bromoalkane. The final compounds serve as raw materials for organic synthesis as well as in the preparation of biologically active substances.

Description

The present invention relates to N, N'-bis-alkylmethyl-1-l-1-propane-diamines of the general formula

where R represents an alkyl chain having from 8 to 14 carbon atoms, and a process for the preparation of these compounds from N, N'-dimethyl-1,2-propanediamine apr. -bromoalkane.

Finally, the compounds serve as raw materials for organic synthesis as well as for the preparation of biologically active substances. 216439 3

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

r - CH 2 - cp - - R CH 3 CH 3 CH 3; wherein R represents an alkyl chain having from 8 to 14 carbon atoms and a process for preparing the same.

Compounds of this type serve as starting materials in the preparation of biologically active compounds such as organic ammonium salts, amine oxides and the like.

So far, only tetramethyl and tetraethyl derivatives of 1,2-propanediamine are known. The compounds of the invention are novel, not previously described in the chemical literature.

Some methods of preparing tetramethyl and tetraethyl denatases are based on the reaction of 1,2-propanediamine and formic acid and formaldehyde (reductase methylation) or from the reaction of 1,2-dibromopropane with diethylamine, but in both cases; the reaction products are mixed in nature and the extracts are very low. and

The process of the present invention is based on N, N'-dimethyl-1,2-propanediamine which, by reaction with the appropriate 1-bromoalkane, yields high purity N, N'-bis (alkylpietyl) -1,2-propanediamine. In the Examples, selected compounds of the invention and a typical method for their preparation are disclosed. The examples do not limit the scope of this method. EXAMPLE 1 0.25 moles of N, N'-dimethyl-1,2-propanediamine are dissolved in dry benzene, heated to reflux, and 0.5 mol of 1-bromononane is added slowly over 1 hour. After all the alkylating agent has been added, the reaction mixture is heated for a further 6 hours under low flow. After cooling, benzene was distilled off, dry ether was added and the mixture was filtered. Concentrated hydrochloric acid is added to the filtrate, the layers are separated, and the aqueous is liberated by reaction with sodium hydroxide. The amine is extracted with ether, the extracts are dried over anhydrous sodium sulfate, filtered, the solvent is distilled off and the product distilled. This gives Ν, β-isopropyl (methylnonyl) -1,2-propanediamine, m.p. 250-253 ° C; η2θ = 1.5422; Rf = 0.63 (acetone: 1 N HCl (1: 1), Silufol, Dragendorf reagent detection); yield 39% of theory. Example 2 jj '

The working procedure is the same as in Example J except that 1-bromo-V is used in the reaction; radekan and the solvent was dry toluene. The product is N, N ' -bis (methyltetradecyl) -1,2-propanedione4 min with mp 55-60 ° C; Rf = 0.48; yield 29% of theory. All compounds of the invention have been identified by elemental analysis and spectral methods.

Claims (2)

11, N, N'-bis (alkylmethyl) -1,2-propanediamines j having the general formula t I R - (i - CH 3 - C 3 H -) - R CHj CHj CHj - where π represents an alkyl chain having a number of atoms of 8-14. 2. A process for the preparation of the compounds of the formula I according to claim 1, characterized in that N, N'-dimethyl-1,2-propanediamine of the formula I is reacted. V ^! . with 1-bromoalkane containing from 8 to 14 carbon atoms in the chain in dry benzene or toluene at the boiling point of the solvent.