CS269698B1

CS269698B1 - / 1,2,2,6,6-pentamethyl-4-piperidyl / 2-propanone

Info

Publication number: CS269698B1
Application number: CS1589A
Authority: CS
Inventors: Peter Rndr Danko; Alojz Balogh; Frantisek Rndr Csc Vass
Original assignee: Danko Peter; Alojz Balogh; Vass Frantisek
Priority date: 1989-01-02
Filing date: 1989-01-02
Publication date: 1990-04-11
Also published as: CS269699B1; CS8900015A1

Abstract

Riešenie sa týká /1,2,2,6,6-penta- ; s metyl-4-piperidyl/-2-propanonu a spósobu je-‘ ho přípravy metyláciou /2,2,6,6-tetrametyl- i -4-giperidyl/-2-propanónu při teplote 20 až i 120° C, připadne v přítomnosti organického rozúšíadla, pri teplote 42 až 120° C v uzavretom systéme. /1,2,2,6,6-Pentametyl-4- piperidyl/-2-propanón je možné použií ako medziprodukt na výrobu světelných stabili- i zátorov polymérov alebo biologicky účinných látok, vrátane liečiv.The solution relates to /1,2,2,6,6-penta-; s methyl-4-piperidyl/-2-propanone and a method for its preparation by methylation of /2,2,6,6-tetramethyl- i -4-piperidyl/-2-propanone at a temperature of 20 to 120° C, or in the presence of an organic solvent, at a temperature of 42 to 120° C in a closed system. /1,2,2,6,6-Pentamethyl-4- piperidyl/-2-propanone can be used as an intermediate for the production of light stabilizers of polymers or biologically active substances, including drugs.

Description

EN 269 698 B1 1

The invention relates to (1,2,2,6,6-pentamethyl-4-piperidyl) -2-propanone (X)

O

and the method of its preparation. [1,2,2,6,6-Pentamethyl-4-piperidyl] -2-propanone is the intermediate for the preparation of high performance polymer light stabilizers as well as for the preparation of biologically active substances, including drugs. From the literature and industry, 1,2,6,6-pentamethyl-4-piperidone is known as one of the starting products for the production of high-efficiency light stabilizers.

Its synthesis by methylation of 2,2,6,6-tetramethyl-4-piperidone with methyl halide is in a liter / 3. Org. Chem. 14, 530, 1949; JP 147 769, 1981 / Detailed Description.

A novel polyalkylpiperidine derivative, 1,2,2,6,6-pentamethyl-4-piperidyl / 2-propanone of formula (I), and a process for its preparation by methylation (2,2,6,6-tetramethyl-4-piperidyl) has now been found. 2-propanone with methyl halide at a temperature of 20 to 120 ° C above 42 ° C in a closed system, optionally in the presence of an organic solvent. The 1,2,2,6,6-pentamethyl-4-piperidyl] -2-propanone of the formula X according to the invention can be used as an intermediate for the production of light stabilizers suitable for polymeric thermoplastic substrates such as polyolefins, polyesters, polyethers, polyurethanes, polystyrenes and others. and also as an intermediate for the production of biologically active substances.

The following examples illustrate, but do not limit the invention. Example 1

A mixture of 8.4 g (0.04 mol) of (2,2,6,6-tetramethyl-4-piperidyl) -2-propanone and 56.8 g (0.4 mol) of methyl iodine was allowed to stand in a sealed reaction vessel 72 hours at room temperature. After completion of the reaction, the hydroiodine formed was precipitated with diethyl ether, the precipitate was filtered off and basified with 20% NaOH solution. The product was extracted from water with n-hexane. The solution in n-hexane was dried with anhydrous sodium sulfate. After filtering off the sodium sulfate and distilling off the n-hexane, 1,2,2,6,6-pentamethyl-4-piperidyl] -2-propanone was obtained as a slightly colored liquid.

Elemental analysis for CjjHjjNO / 211,350 /

Calculated: 73.88% C, 11.92% H

Determined: 73.62% C. H, 11.75;

6.63% N6.75% N IR, solution in CCl4: 2,965, 2,935, 2,890, 2,845 '(5 / CH); 1735 - Al (c = 0). 1410 - Z / c-N /; cm'1

Claims

1 H-NMR spectrum, solution in CDCl 3: 2.22-singlet Z 3 H, N-CH 3; 2.13 - doublet / 2H /, CH 2 CO; 2.07 - singlet (3H), CO-CH 3; 1.17-1.04 - doublet / 12H / gem.CH3 = 1.75-0.33 - multlplet / 5H /, circular, CH; (ppm) Example 2 A mixture of 9.85 g (0.05 mol) of [2,2,6,6-tetramethyl-4-piperidyl] -2-propanone, 28.4 g (0.2 mol) of methyl iodine and 50 ml The methanol was heated in a sealed glass vial of 100 mL for 5 hours at 120 ° C. After the reaction was complete, the reaction mixture was cooled to room temperature and methanol was distilled off after opening the vial. The resulting hydroiodine sapremyl diethyl ether was basified with aqueous KOH and the product was extracted with n-heptane. After drying the solution with sodium sulphate and distilling off n-heptane, 1,2,2,6,6-pentamethyl-4-piperidyl / -2-propane was obtained as a misty liquid. INVENTION 1. [1,2,2,6,6-Pentamethyl-4-piperidyl] -2 = propanone of Formula IO

2. A process for the preparation of 1,2,2,6,6-pentamethyl-4-piperidyl] -2-propanone of the formula I according to claim 1, wherein: 2,2,6,6-tetramethyl-4-piperidyl The 2-propanone is reacted with methyl halide at 20 to 120 ° C, optionally in the presence of an organic solvent.

3. Process according to claim 2, characterized in that the reaction is carried out at a temperature of 42 to 120 ° C in a closed system.