SU265887A1 - Method of obtaining piperazine derivatives - Google Patents

Description

This invention relates to a process for the preparation of piperazine derivatives of the general formula

/ Hl

 -C-CH -N fi-s

GU

where X is hydrogen, halogen;

Y is hydrogen, halogen, OCH3.

The compounds exhibit high physiological activity and can be used in the pharmaceutical industry.

According to the invention, the process for the preparation of piperazine derivatives is the interaction of N-phenacylpiperazine with an acid chloride in an aqueous or organic-aqueous medium, and the product obtained as a hydrochloride is converted into the base in the usual way.

Example 1. To a solution of 5.5 g (0.02 mol) of M- (-chlorophenacyl) -piperazine hydrochloride in a minimum volume of warm water was added 10 ml of a 20% sodium hydroxide solution and 30 ml of benzene. Thoroughly shake to transfer the entire K - ("- chlorfenacil) piperazine to benzene.

A solution of 3.32 g (0.021 mol) of l-fluorobenzoyl chloride and 20 ml of benzene is added and shaken for 10 minutes. Allow to stand, separate the benzene layer, saturate it with dry hydrogen chloride. The product is separated and crystallized from methanol, precipitated with ether. Obtain 3.45 g (87%) of colorless crystals of hydrochloride N- (l-chlorfeiacyl) -Y - (/ gfluorobenzoyl) piperazine, so pl. 210 ° C. Found,%: C 58.40; H 4.96; N 7.12.

CigHigCbFNsOa.

Calculated,%: C 58.59; P 4.82; N 7.06.

Example 2. 2.04 g (0.01 mol) of N-phenacylpiperazine is dissolved in 10 ml of water, 10 ml of 10% sodium hydroxide solution and 1.55 g (0.011 mol) of beisoyl chloride are added. Shake 10 min. 50 ml of benzene is added and the product is extracted into the benzene base. The benzene layer is separated and saturated with dry hydrogen chloride to form a product precipitate. The precipitate is crystallized from ethanol. The output of 2.62 g (76%), so pl. 174 ° C.

The base separated after acylation can be treated with an ethanol solution of hydrogen chloride.

Claims (8)

Found,%: C 65.78; H 6.24; N 7.98. 1.Y- (-Fluorophenacyl) -M-benzoylpiperaz hydrochloride. Output 82%, so pl. 219 ° C. Found,%: C 62.71; H 5.64; N 7.30. CigHaoClNaOsCalculated,%: C 62.86; H 5.52; N 7.22. 2.N- ("-Fluorofenacil) -N- (p-fluorobenzene piperazine hydrochloride. Yield 85%, t. 237 ° C; Found: C 59.70; H 5.20; N 7.16. CisHigClFNzOa. Calculated, %: C 59.89; H 5.03; N 7.35. 3.Y- (i-Fluorofenacil) -N- (w-fluorobenzoyl piperazine hydrochloride. Yield: 79%, t. 224 ° C; Found: C, 60.03; H, 5.12; N, 7.40. CigHigClFNaOs. Calculated, %: M 59.89; H 5.03; N 7.35. 4.N- (l-Fluorofenacil) -Y- (l-chlorobenzoi piperazine hydrochloride. Yield 83%, t. 211 ° C. Found,%: C 60.11; H 5.01; N 7.31. CigHigClFsNaOa. Calculated ,%: C 59.89; H 5.03; N 7.35. 5.N- (l-Fluorofenacil) -N - (l-chlorobenzene piperazine hydrochloride. Yield 84%, t. 119 ° C. Found,%: C 57.41; H 4.66; N 7.11. CisHisCbFNsOa. Calculated ,%: C 57.58; H, 4.82; N, 7.05. 6.M- (l-Fluorofenacil) -Y- (W - chlorobenzo piperazine hydrochloride. Yield 90%, t. 205 ° C Found,%: C 57.44; H 4.95; N 7.20. CigHigClsFNsOs. Calculated, %: C 57.58; H, 4.82; N, 7.05. 7.Y - ((g-Fluorofenacil) (o-chlorobenzoyl) piperazine hydrochloride. Yield 68%, so pl. 257 ° C. Found,%: C 57.90; H 4.86; N 7.16. CigHigCUFNsOs. Calculated,%: C 57.58; H 4.82; N 7.05. 8.Y- (p-Fluorofenacil) -M - ("-methoxybepsoyl) -piperazine hydrochloride. Output 81%, so pl. 165 ° C. Found,%: C 61.16; H 5.58; N 6.97. C2H22ClFN2O3. Calculated,%; C, 61.21; H 5.64; N 7.13. The invention The method of obtaining piperazip derivatives of the formula: where X is hydrogen, halogen; Y is hydrogen, halogen, OCHN, characterized in that the N-fepacylpiperazine is treated with chlorine anhydride of the acid in an aqueous or aqueous organic medium and the resulting product in the form of hydrochloride is converted into the base in the usual way.