SU367103A1 - METHOD OF OBTAINING - Google Patents

Description

Consequently, it is a process for the preparation of e-aminos in the literature of a-aminosyl types of selenophen.

These compounds are of interest as substances with physiological activity.

A known method for the preparation of a-aminosyrts by the interaction of the corresponding halokethoia with A. imyom followed by the reduction of the amino ketone formed by a known procedure.

In order to obtain undescribed aaa.I1 alcohols, a series of selenofen is subjected to condensation (o-bromoketholes of a series of selenophen, for example, bromoacetoselenofen, with secondary achmina in a medium of organic solvent, followed by reduction of the resulting α-aminoKetone, are known. product obychyyn.mn techniques.

The yield, constants and results of the analysis of the obtained ac-siamines and their hydrochlorides are given in the table.

Example 1. Synthesis of 2- (a-hydroxy-p-dimethylamipoethyl) -selenofine.

1. 2- (and - (bromoaceto) - selenophen.

To a solution of 30 g (0.12 g-mol) of 2-acetoselenofen in a mixture of 70 ml of ether and 35 ml of dioxane, 36.8 g (0.23 g-mol) of bromine are added over 40 AIUH at 20 ° C. The reaction mixture is moved at 20 ° C for another 40 minutes and poured into 1: 1 ether-water (65 ml each). Ether) The 1st layer is separated, washed several times with water and dried with sulphate

on three . After} evaporation of the ester, 27 g (69%) of 2 - (w-bromoaceto) - selenophene were obtained.

T. 1PL. 48-49 ° C (from methanol).

2. 2 - (a - hydroxy - p - dimethylamioethyl) selenophen.

To a solution of 18 g (0.4 g-mol) of dimethylamine in benzene (the solution is obtained from 32.5 g of hydrochloric acid dimethyl mine by reaction with a saturated aqueous solution of alkali at

0 ° C and subsequent extraction with 200 mg of benzene; dried over potash) a solution of 20 g (0.08 g-mol) of 2 - (w - bromoaceto) selenofey in 120 ml of dry benzene is added in 20 minutes while moving. The mixture is left on

10 hours The precipitate is sucked off, washed with benzene. The benzene solution was treated with 2N hydrochloric acid, the aqueous layer was separated, made alkaline with a saturated aqueous solution of soda, the ammonium ketone extracted as an oil was extracted with ether.

The potash-dried ether solution is evaporated in vacuo to a volume of 100 ml and added in 1 pass with stirring) pm to 3.8 g (0.1 g-mol) of lithium aluminum hydride in

100 ml of absolute ether. The mixture is boiled

Table

 Outputs

3 hours, cooled, decomposed with water. The precipitate is sucked off, washed with ether. The filtrate is treated with 2N hydrochloric acid, the aqueous layer is alkalinized with aqueous alkali and extracted thoroughly with ether. The precipitate from the filter is dissolved in 2N hydrochloric acid, 32 g of acid is added to the solution and, after basification with an alkali solution, it is thoroughly extracted with ether. The combined ethereal solution is dried in m. After distilling off the solvent and distillation in vacuum, 2.1 g of 2- (a-0 | Xi-p-dimethylaminoethyl) - selenophen was obtained.

2 - (a-hydroxy - p - d. Methylaminoethyl) -selenofen hydrochloride is obtained by reacting dry hydrogen chloride with a solution of hydroxylamine in absolute ether. The output is quantitative. Recrystallized from dry acetone.

Example 2. Synthesis of 2 (a-hydroxy-p - (- pi1-peridinoethyl) - selenophene.

To a solution of 3.4 g (0.04 g-mol) of pilyridium in 10 ml of dry ether, a solution of 5 g (0.02 g-mol) of 2 - (co-bromoacetone) - selenophen in 30 ml is added over 15 minutes with stirring dry ether is left for 10 hours. The precipitate is filtered off with suction and washed with ether. The combined ethyl acetate solution is treated with 2N hydrochloric acid. The aqueous layer is alkalinized with a saturated aqueous solution of soda, extracted with ether and dried with potash.

The resulting amino ketone was not isolated, the solution was evaporated in vacuo to a volume of 50 ml, and the mixture was added, with stirring, for 30 compounds given, given on the starting bromketone. Chlorohydrates are quantitative. 40 min to 0.5 g (0.013 g-mol) of lithium aluminum hydride in 35 L1L absolute ether. Kip t 3 hours, decompose water. The precipitate is filtered off with suction, the filtrate is taken up in 2N hydrochloric acid, the aqueous layer is made alkaline with an alkali solution and the mixture is thoroughly extracted with ether. The precipitate is also treated with 2N hydrochloric acid until complete dissolution, 4 g of tartaric acid is added to the solution, alkalized with aqueous alkali and thoroughly extracted with ether. The combined ethereal extracts are dried by potash. After evaporation of the solvent in vacuo, 1, g of 2-a-hydroxy-p- (n 11 -peridinoethyl) - selenophene was obtained. The subject of the invention is a process for the preparation of o-amino alcohols containing a selenyl radical, characterized in that a co-bromoketone of a series of selenophene, for example, co-bromoacetoselenofen, is subjected to condensation with a secondary amiome in an organic solvent followed by reduction of the resulting a-a-amino ketone in a known manner and isolating the target product with conventional methods.