SU505358A3 - The method of producing piperazine derivatives - Google Patents

Description

This invention relates to a process for the preparation of new piperazine derivatives which possess biological activity and can be used, for example, in medicine. A method of producing ethers is known in organic chemistry, for example, by alkylation of the corresponding alcohols. Alkylating agents used are alkyl halide or diphosphate or N-toluenesulfonic acid ester. Describes a method for the preparation of piperazine derivatives of the general formula, based on the reaction known in organic chemistry, where OR is lower alkyl; N is lower alkylcarbamoyl, lower alkyl; d - hydrogen atom, lower alkyl. or their salts, concluding that the compound of the general formula O 5 is as defined above; process the corresponding alkylating or acylating. agents, followed by isolation of the desired product by a known technique in the form of a base or salt. As an alkylating agent, usually the lower alkyl halide, di (lower) alkyl sulfate, sulfonic acid ester in the presence of alkali are used. It is also possible to first replace the OH-group with a chlorine atom with the aid of chlorinating SOCl, and using an agent such as PC1 or the resulting compound, to react with an alkaline alcohol. The introduction of the acyl group is carried out by means of a suitable acylating agent, for example, an acid chloride, carbamoyl chloride, anhydrite. Example. 1-H1-4-imidazolidinon- (2) -ylphenyl-X-acetyloxyethyl-4- (2-methylphenyl-piperazine or its chloride 7.6 g (O, O2 mol) 1- | 1-4-amidazolidinone- {2 ) -ylphenyl-l-hydroxyethyl-4- (2-methylphenyl) -piperazine, 2.5 ml of acetic anhydride and 76 ml of chloroform for more than 2 hours and refluxed. After distilling off the solvent, the residue crystallized with ethanol was dissolved in chloroform and extracted by shaking with a solution of potassium carbonate and water. The organic phase is dried with sodium sulfate and the chloroform is distilled off. The residue obtained is crystallized in ethanol. Chloride is obtained from the base in hot ethanol after addition of concentrated hydrochloric acid. Salt after re; 11 installation from ethanol has so pl. 31О С (decomposition). The yield is 5.5 g. EXAMPLE 2 1-G1-4-im1chazolidino n- (2) -ylphenyl -1-methy carbamoyloxyethylT.-4- (2-methylphenyl) -hyperazine or its chloride . 7.6 g (0.02 mol) 1- | 1- 4-imidazolidinone- (2) -ylphenyl) -1-hydroxyethyl-4- - (2-methylphenyl) -piperazine, 1.1 ml of methyl isocyanate and 114 ml of chloroform a. for 1 hour at 60-70 ° C, shake into a montage. After the distillation of chloroform, a residue remains which is crystallized in ethanol. Chloride is obtained from the base in hot ethanol by the addition of ethanolic hydrochloric acid. Salt after. recrystallization from ethanol has an mp. (decomposition ). The yield is 7.5 g. EXAMPLE 3. 1-G1-4-imidazolidinone- (2) -ylphenyl -1-ethoxyethyl 1.-4- (2-methylphenyl) piperazine. To a solution of 1.84 g (0.08 mol) of sodium in 200 ml of absolute ethanol was added 8.7 g (O, O2 mol) chloride l-Jl- | 4 imidazolidinon- (2) -klfenkl -1-x 3THnJ -4- (2-methylphenyl) -liperazine, resulting in a short-circuit of the corresponding hydroxy compound by -chlorination with PC1 in acetonitrile. After stirring for 1 hour at 40 ° C, the calculated amount of ethanolic hydrochloric acid is added, sucked off from precipitated NaCl and the ethanol is distilled off, leaving only 20 ml. A base is obtained from the residue. A base in ethanol with a calculated amount of methanesulfonic acid gives the methanesulfonate of the above compound. Similarly, the following compounds / A-N S-H BgC-SNg-Sn- / A. x%. „About gC -CH, / - and HHf UI - H„ I I n “2C-sn, H-Q K -N-H n, s-сн. H HC-CH, Of VH

f O-CHrCH / -V /%

0

HtC -CHi

one

0 D

, -CH, -CH, -CHHQK / VH

HjC-CH,

CH-CH.-K

OR

 where K is lower alkyl;

m - lower alkylcarbamoyl, lower

acyl; K. - hydrogen atom, lower alkyl,

or salts thereof, characterized in that the compound of the general formula

Wl-CH,

CH

P -1 GL4n-sn- /

1- | 1-4-imidazolidinone- (2) ylphenylZ-1-n. utilcarbamoyloxyethyl-4- (2-methylphenyl) -Pig (naphazine; t, pl. 127 ° C (decomposition).

invention formula

Claims (4)

1. A method for producing piperasin derivatives of the general formula N.S. has the above meaning treat with an appropriate alkylating or acylating agent followed by isolation of the target product by a known technique as a base or salt; 2. The method according to p. 1, about tl and h and y and that with the use of the corresponding lower alkyl halide, di (lower) alkyl sulfate, sulfonic ester ester as the alkylating agent.  3. The method according to paragraphs. D and 2, that is, that the reaction is carried out in the presence of alkali. 4. The method according to claim 1, of which is tl and h and yc in that the acid chloride, carbamoyl chloride is used as the acylating agent.