SU435234A1 - Method of producing derivatives of 2,2,6,6-tetramethyl piperidine - Google Patents

Description

one

This invention relates to a process for the preparation of new compounds that may find application in the polymer industry.

A method based on the known method of acylation of alcohols with acid chlorides is proposed for the preparation of 2,2,6,6-tetramethylnineridine derivatives of the general formula

OOS1SYU S (SbN5) 2

sn

TO

SN

I

R

where R- N, O,

the fact that the corresponding sirt of the general formula

(sn,) „he

 Lch

ъ

/

ns

sn.

where R has the above meaning; n 0.2.

subjected to interaction with acid chloride | 3, p-diphenyl-a-cyanoacrylic acid in the medium of an organic solvent in the presence of triethylamine, followed by isolation of the target product lime method. The yield of 70-75%.

Example 1. 2,2,6,6-Tetramethyl-4-piperidyl-p, |: 5-diphenyl-a-cyanoacrylate.

3.9 ml of triethylamine are poured into a solution of 4.45 g of 2,2,6,6-tetramethyl-4-hydroxypiperidine in 50 ml of absolute dioxane, then 6.2 g of α-cyano-r chloride, diphenyl acrylic acid are added dropwise, the mixture is moved 2 hours at room temperature and 1 hour at 60-70 ° C, triethylamine hydrochloride is filtered off, the solvent is evaporated in vacuo, and the solid residue is non-recrystallized from ethanol. Obtain 7 g (70% of theory) of the product in the form of colorless crystals, so pl. 106-107 ° C (from ethanol).

Found,%; C 77.32; H 7.22; N 7.24.

C25H28N202.

Calculated,%: C 77.30; H 7.28; N 7.34. Example 2. 2,2,6,6-Tetramethyl-4-piperidyl-1-oxyl- | 3, p-diphenyl-a-cyanoacrylate.

This compound is prepared under the conditions of Example 1 from 4.6 g of 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl and 8.11 g of acid chloride p, rdiphenyl-a-cyanoacrylic acid. Output 7.5 g (72% of theory); m.p. 142-143 ° C.

Found,%: C 74.42; H 6.74; N 6.94.

C25H27N2O3.

Calculated,%: C, 74.98; H 6.75; N 7.01.

Example 3. 2,2,6,6-Tetramethyl-4-piperidyl-p-ethyl-p, p-diphenyl-.a-cyanoacrylate.

To a solution of 1.8 g of 2,2,6,6-tetramethyl-4-p-hydroxyethylpiperidine in 50 ml of absolute tetrahydrofuran, 2.5 ml of triethylamine are poured, and then 2.5 g of the acid chloride p, p-diphenyl-1-cyanoacrylate is added dropwise acids in 20 ml of absolute tetrahydrofuran. The mixture is stirred for 12 hours at room temperature, the triethylamine hydrochloride is filtered off and the solvent is evaporated in vacuo. Obtain 3 g (70%) of a colorless substance, so pl. 42 ° C (from ethanol).

Found,%: C 79.75; H 7.58; N 6.71.

C27H32N2O2.

Calculated,%: C 78.01; H 7.69; N 6.73.

Example 4. 2,2,6,6-Tetramethyl-4-oxyl-4piperidyl-p-ethyl-p, p - diphenyl-a-cyanoacrylate.

Under the conditions of Example 3, out of 2 g of 2,2,6,6-tetramethyl-1-oxyl-4-p-hydroxyethylpiperidine and 2.5 g of the acid chloride p, p-diphenyl-a-cyanoacrylic acid, 3.5 g (75 g) are obtained. % of theory) of a paramagnetic substance in the form of pink crystals, so pl. 58 ° C.

Found,%: C 75.14; H 7.05; N 6.38.

CajHsiNaOs.

Calculated,%: C, 75.25; H 7.19; N 6.50.

Subject invention

The method of obtaining 2,2,6,6-tetramethylpiperidine derivatives of the general formula

OOS (SK) S (SbN5) 2

where R is H; O, characterized in that 15 corresponding alcohol of the general formula

(СН2) „ОН

where R has the above meaning; , 2, is reacted with p, p-diphenyl-a-cyanoacrylic acid chloride in an organic solvent in the presence of triethylamine, followed by isolation of the target product in a known manner.