Patent GB-802995-A (GB)
Title: Fatty acid amides and derivatives thereof
Inventor: BRUCE WILLIAM FAUSSET
IPC: C07C237/00
Filed: 1956-12-24
Abstract: The invention comprises free or esterified alkanolamino-bis-(fatty acid amides) of the general formula <FORM:0802995/IV (b)/1> and salts thereof, wherein X and Y represent divalent alkylene radicals of 1 to 7 carbon atoms, R1 and R3 are alkyl or alkenyl radicals, R2 and R4 are alkyl, alkenyl, aralkyl or arylhydroxyalkyl radicals wherein the aryl group is a phenyl group or an alkyl-, alkoxy-, hydroxy-, halogeno-, nitro-, amino- or mono- or di-alkylamino substituted phenyl group and R5 is a hydroxyalkyl or esterified hydroxyalkyl radical of 2-4 carbon atoms, and comprises also processes for the preparation of alkanolamino-bis-(fatty acid amides) by heating a compound of the formula R6NH2 with at least two molecular proportions of a halogeno acylamide of the formula <FORM:0802995/IV (b)/2> or by heating a compound of the formula <FORM:0802995/IV (b)/3> with a halogeno-acylamide of the formula <FORM:0802995/IV (b)/4> wherein Hal is a halogen atom and R6 is a hydroxyalkyl group of 2-4 carbon atoms. The above reactions are preferably carried out at a temperature in the range 80 DEG  to 200 DEG  C.  If desired, the hydroxyl group of the alkanolamino-bis-(fatty acid amide) products may subsequently be esterified.  Preferred products are compounds wherein the total number of carbon atoms in R1, R2, R3 and R4 is from 12 to 26 and none of these radicals has more than 12 carbon atoms; suitably R1 and R2 are each alkyl or alkenyl radicals of 2 to 6 carbon atoms and R3 and R4 are alkyl radicals of 4 to 6 carbon atoms.  Preferred products include the bis-(N : N-di-n-amyl)-, bis-(N : N-di-n-butyl)-, bis-(N : N-di-isobutyl- and bis - (N - methyl - N - o  - phenyl - tert.-butyl)-derivatives of bis-carbamoylmethyl-beta - hydroxyethylamine; 1 : 11 - diphenyl - 2 : 2 : 3 : 9 : 10 - pentamethyl - 4 : 8 - diketo - 6 - (betahydroxyethyl) - 3 : 6 : 9 - triazaundecane, N : N - bis - (N - methyl - N - o  - phenyl - tert. - butyl-carbamoylmethyl)-b -methyl-b -hydroxyethylamine; N : N - di - (N - methyl - N - o  - phenyl - tert. - butyl - carbamoylmethyl) - 1 - ethyl - 2 - hydroxyethylamine; 2 - hydroxy - n - propylamino - bis - (N : N - di - n - acetamide) and g  - hydroxy - n - propylamino - bis - (N : N-di-isobutyl acetamide).  Many other examples are given, the products being isolated in the form of the free base or as salts such as the hydrohalide, acetate, sulphate, oxalate, tartrate, picrate, phosphate, propionate and succinate.  Halogeno-fatty acid amides of the formula Hal-X-CO-NR1R2 are made, for example, by treating a chloroacyl chloride of the formula Cl-X-CO-Cl with an amine of the general formula R1R2NH.  The preparation of N : N-diamyl-, N : N-di-n-butyl-, N : N-di-idobutyl- and N : N - di - allyl - chloracetamide by the above method is described. Alkanolamino-fatty acid amides of the formula R6-NH-Y-CO-NR3R4 are made, for example, by treating a chloro-acylamide of the formula Cl-Y-CO-NR3R4 with an alkanolamine of the formula R6NH2.  The preparation of b -hydroxyethylamino - N - methyl - N - o  - phenyl - tert. - butyl acetamide by this method is described.