SU490282A3 - Method for producing alkanolamine derivatives - Google Patents

Description

PrNH- VoCHgCHOHCHR NH,

III

where R R% R and R have the meanings given above, or a salt of this amino derivative with an acid, is reacted with a carbopolymer compound of the general formula RCOR, where R and R have the same motions as stated above.

Drainage interaction is reduced under reducing conditions. The desired product is isolated as a free base or salt. Reduction conditions suitable for the reaction are provided by the presence of hydrogen and hydrogenation catalysts (e.g. platinum) in an inert diluent or solvent (e.g. water or ethanol) and / or in the case where the carbonyl compound used as the starting compound contains the radical R, which is an alkyl group, is taken in excess. Reductive recovery is also achieved if an alkali metal borohydride, for example sodium borohydride, is present in the reaction mixture, and the reaction is carried out in an inert diluent or solvent selected from grouped solvents, which includes water, methanol, ethanol and an excess of carbonyl compound used as a source of VN1, estva.

As suitable salts of alkanol derivatives, for example, the sun obtained by HJMI using inorganic acids, for example hydrochlorides, hydrobromides, phosphates and sulfates, as well as salts based on organic acids, for example oxalates, lactates, tartrates, acetates, salicylates, citrates, benzoates, p-naphthoates, adinates or. 1,1-methylen bis- (2-hydroxy-3-naphthoates); iLiH is the same salt, but obtained using synthetic resins with acidic properties and, in particular, sulfonated polystyrene resins (nanopolymer, sulfonol styrene resin | s).

In all nimers, the substances used are taken in parts by weight.

P) Example 1. A mixture of 1 part of 1- (2-ethnl-4-pron; 1-namidophenoxy) -3-amnno-2-propanol, 20 parts of water, 10 parts of acetone and 0.3 parts of platinum was shaken in hydrogen atmosphere under a pressure of 2.5 atm for 12 hours. The resulting reaction mixture was filtered and the filtrate was vacuum-diluted by the node until half the original volume of liquid was left. To the remaining solution was added 5 parts of sodium chloride, and the mixture was extracted with 50 parts of ethyl acetate. The ethyl acetate extract was evaporated to dryness, and the residue was treated with 10 parts of diethyl ether. The resulting mixture was filtered and

the precipitate on the filter was transferred from ethyl acetate. Thus, 1- (2-ethyl-4-propionamidophenoxy) -3-isopropylamino-2-pronanol with m.p. 136C.

Example 2: 0.3 parts of sodium borohydride was added over 10 mil to a stirred mixture of 1 part 1- (2-ethyl-4-proiopamidophenox) -3-amio 2-propanol, 20 parts of acetone and 20 parts of water. The resulting mixture was infused from the original volume. As a result, 1- (2 ethyl-4-nropionamidophenoxy) -3-isonronylamino-2-nropanol with so-called nl was obtained. 136C.

Example 3. The procedure described in Example 2 was repeated for the fact that

instead of 1- (2-ethyl-4-propiopamidophenoxy) -3-amino-2-propanol, the appropriate

1-feioxy-3-amino-2-pronanol derivative.

Thus, the compounds shown in the table were obtained.

B-C-NK-H / VoCH.CHOHCH TyiHCHlCHOo

about

40

50

55

Example 4. The method of the method described in Example 1 or Example 2 is repeated except that instead of acetone, cyclopentap or methyl ethyl ketone are replaced. 1- (2-ethyl-4-propionamidophenoxy) -3-cyclopentylamino-2-propanol is obtained; m.p. 132-134 ° C and, respectively, 1- (2-ethyl-4-propionamidofoynoxy) -Z-fluorobutylamio-2-nropaiol.

P r with d m s t. II 3 about b and e and u

The method of obtaining alkanolamine derivatives of the general formula

to

ifNH - / VoCH, .- CHOHCHR fiHCHRR BII

where R is hydrogen or alkyl Cj-Cz;

R is hydrogen or alkyl containing up to 8 carbon atoms, which may be substituted by one or two substituents selected from hydroxy groups, alkoxy groups containing up to 5 carbon atoms, as well as phenyl and phenoxy groups, which may in turn be replaced by one or more chlorine or bromine or methyl, ethyl, methoxy or ethoxy groups, or

R and R together with the adjacent carbon atom form a cycloalkyl radical containing up to 8 carbon atoms;

R2 - formyl, alkanoyl, tsikloalkilkarbolil, aralkanoyl aralkenoil or ariloksialkanonl, each of which contains up to 10 carbon atoms which may be substituted by one or more halogen atoms or alkyl having up to 4 carbon atoms or galoidalkanoil, alkenoyl alkanesulfonyl or alkoxycarbonyl, each

113 of which contain up to O carbon atoms;

R is alkyl containing up to 10 carbon atoms;

R and R are the same or different and represent hydrogen or alkyl containing up to 4 carbon atoms;

or their salts, from.and / chjazhti-.h so that the compound of the formula

.snonszh N

 3 R

where R-, R R and R are as defined above, are reacted with a carbonyl compound of the formula RCOR,

where R and R are as defined above, under the reaction conditions, followed by separation of the target product in a known manner as a free base or a salt.

2. Particularly in paragraph 1, characterized in that the process is carried out in the presence of hydrogen and a hydrogenation catalyst in an inert diluent or solvent.

3. The method according to claim 1, characterized by the term that

The process is carried out in the presence of an alkali metal borohydride in an inert diluent or in a solvent.