SU388551A1 - The method of obtaining 6-alkyl-7- (alkylaminoacylamino) benzodioxanes-1,4 - Google Patents

Description

(54) METHOD FOR OBTAINING 6-ALKYL-7- (CO-DLKYLAMINOACYLAMINO) -BENZODIOX., 4

one

The invention relates to a method for producing novel benzodioxane derivatives not described in the literature, which have pharmacological activity.

A known method of producing B-dialkylaminoethyl esters of 5- and 6-carboxybenzodioxano & -1 i4 by condensation of chlorohydrin D 5 and 6-carboxybenzodioxanes-1,4 with amino alcohols,

However, in the literature there are no reports on the preparation of 6-alkyl-7- (Sh-alkylamino-acylamino) benzodioxane -1.4j, which has valuable properties.

According to the invention, a method for the preparation of 6-alkyl-7- (UU-alkylamino-acylamino) benzodioxanes-1,4 is described, in which 6-alkyl benzodioxane-1,4 is nitrated with diluted nitric acid, the resultant 6-alkyl-7-nitrobenzodioxane -1, 4 are reduced with iron and hydrochloric acid in an alcohol solution to O-apkpg-7-aminobenzodioxane-1,4, which is acylated with chloroanhydrides (Jj-chloroalkanoic acids in a toluene solution, and the resulting 6-alkyl-7- (OU-chloroacylamino ) -benzodioxanes-1,4 are reacted with amines in an alcohol solution.

Example: Preparing an emulsion of 1.3 gm mol of the corresponding 6-alkylbenzodioxan-1, 4 (1) and 240 ml of water, transfer at 2 ° -5 ° C, and add 180 ml of a 56% blend over 1 hour. acido Then stirred for 1 hour at the same temperature, extracted with benzene at 2O С | the extract is washed with water, distilled and get:

b-Ethyl-7-nitrobenzodiox No.-1,4, yield 70%, bp. 159-161 ° С (5 mm of mercury, st.); t pl "4O-41 C (from 80% ethanol)

6-Bugil-7-nitrobenzodioxan-1,4; yield 80%; bp 181-183 ° С (5 mmHg. Mp. 57-58 ° С (from 8O% ethanol).

0.4 g mol of the corresponding nitro derivative was dissolved in 1000 ml of 80% ethanol, 14O g of iron powder, 10 g of copper chips were added and 28 ml of concentrated hydrochloric acid was added with stirring and boiling point. Stirring and boiling are continued for another 3 hours, the hot solution is filtered or cold sludge, the filtrate is cooled to 20 ° C, acidified with hydrochloric acid, ethanol is distilled off, the residue is alkalinized with sodium hydroxide, extracted with benzene, the extract is distilled and obtained; 6-Ethyl-7-aminobenodioxan-1,4; vy14O-142 with (5 mm of mercury.) stroke 80%} t, kip. l jtl, pl. 44-45 C (from heptane); m.p. hydrochloride 22O-222 C (with decomposition from ethanol). 6-Butyl-7-aminobenzodioxan-1,4; yield .75%; g. 155-156 С (Змрт.ст.);

6-Alkyl- 7- (CO-chloro-cyclamino) -benzodioxan-1,4 1,5503; m.p. hydrochloride 215-210 C (from ethanol). A solution of 0.11 g mol of the corresponding acid chloride (A-chloroalkanoic acid in 100 ml of anhydrous toluene is added at a temperature not higher than 15 ° C. To a solution of 0.1 O g-mol of the amino derivative in 1OO ml of anhydrous toluene, the mixture is boiled under stirring for 3 us, the solvent is distilled off, the residue is recrystallized from ethanol-water and to obtain b-alkyl-7- (t) - -chloro-ylaino) -benzodioxanes-1,4. The data are given in table. 1. Table 1

four%

A solution of O, O2 g-mol of the obtained compound and 0.04 g-mol of amine (H NRR) in 5 O ml of ethanol was boiled for 8 hours, the ethanol was evaporated to half the original volume, 30 ml of water was added, cooled to 20 ° C, extracted e-rum, the extract is passed through a column filled with 30 g of anhydrous alumina, distilled out.

6 Alkyl-7- (Cf-alkylaminoacylamino) benzodioxanes-1,4

"5 (CHg)

N (

152-153

148-149

133-134

171-172

the finisher and get the target products in the form of bases.

Chlorohydrates are obtained by passing anhydrous hydrogen chloride gas into ethereal base solutions. Reinekates are obtained by adding an aqueous solution of an ester of classed hydrochloride to an aqueous solution of ammonium reinekag. The data of the compounds obtained are given in table. 2

table 2

64-65 (ethanol-water)

103-104

144-145

1.5463

Continued table.