SU482943A3 - Method for producing alkanolamine derivatives - Google Patents

Description

It can be accelerated or completed when heated to 90-100 ° C. The reaction can be carried out at atmospheric and elevated pressures, for example, when heated in a sealed vessel. Inert solvents can be used, for example methanol or ethanol, an excess of amine of the general formula NH 2 R.

The alkanolamine derivatives obtained according to the invention in the form of the free base can be converted into salts of various acids by their usual reaction with the corresponding acid.

Example 1. A solution of 1 g of 1- -carbamine methylphenoxy-2, 3-epoxypropane and 10 ml of isopropylamine in 25 ml of methanol is heated in a sealed tube at 110 ° C for 12 hours. The mixture is evaporated to dryness and the residue is distributed between 50 ml of chloroform and 50 ml of aqueous 2N. hydrochloric acid solution. The acidic aqueous layer is separated, made alkaline with sodium carbonate, and extracted twice with 50 ml of chlorofor / R NHCO - A - /; oHHCHO # 4H, NHB

ma The combined extracts are dried and evaporated to dryness. The solid residue is recrystallized from ethyl acetate. The 1- / g-carbamine methylphenoxy-3-isopropylamino-2-propanol obtained in this way has a mp. 146-148 ° C.

Example 2. A solution of 4 g of p- (3-chloro-2-hydroxypropoxy) phenylacetic acid ethyl ester and 15 ml of isopropylamine in 15 ml of methanol is heated in a fixed tube for 12 hours at 110 ° C. The mixture is evaporated to dryness and the solid residue is partitioned between ethyl acetate and water. The ethyl acetate layer is separated, dried, evaporated to dryness and the solid residue is recrystallized from a mixture of ethyl acetate n non-ether (m.p. 60-80 ° C). The 1- / g-N-isopropylcarbaminomethylphenoxy-3-isopropylamino-2-propanol obtained in this way has a mp. 132-134C.

Example 3. A solution of 1.2 g of 1- (4-p-carbaminetnl-2-methoxyphenoxy) -2.3 - epoxypropane and 10 ml of isopropylamine in 20 ml of methanol is heated under reflux for 16 hours, cooled and evaporated to dryness under reduced pressure. The solid residue is recrystallized from a mixture of ethyl acetate n non-ether (m.p. 60-80 ° C). The 1- (4-p-carbaminoethyl-2-methoxyphenoxy) -3-isopropylamino-2-1-propanol is prepared in this way. 108 - - 109 ° C. Analogously to Example 1, it is possible to obtain the compounds given in the table. The subject of the invention. A method for producing alkanolamine derivatives of general formula 1.

OCH, -CHOH-CH NHR

where R is alkyl or oxyalkyl containing up to 6 carbon atoms;

R2 is alkanoyl containing up to 6 carbon atoms, or carbamoyl, or alkylcarbamoyl, or alkenylcarbamoyl, in which alkyl and alkenyl contain up to 6 carbon atoms, or carbazoyl;

A is alkylene with 1-5 carbon atoms;

 or 2;

Cs - the same or different when

or ZION-CH2Y group,

where Y is halogen, and all other symbols correspond to those stated above, are introduced into interaction with an amine of the general formula NH2R, where R has the values indicated above, followed by isolation of the target product in a known manner in free form or in the form of a salt.

Priority featured:

02.02.69 when:

And in the compound of formula I is methylene .i

10.24.69 when:

And - alkylene contains 2-5 carbon atoms. and mean hydrogen, halo, nitro, OKCI1-, cyano, alkyl, alkenyl, acyl and alkoxycarbonyl containing up to 6 carbon atoms, cycloalkyl, containing up to 8 carbon atoms, alkylthio, alkoxy or alkenyloxygroup containing up to 5 carbon atoms atoms, aryl, aryloxy, aralkyl and aralkoxy containing up to 10 carbon atoms, alkyl containing up to 5 carbon atoms, substituted by one or more hydroxy or alkoxy groups, characterized in that the compounds of general formula II / -CH-CHN