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Synthesis method of hydroxypiperidinone ethylamine salt

A technology of oxypyridone ethylamine salt and synthesis method, which is applied in the synthesis field of oxypyridone ethylamine salt, can solve the problems of long process route of oxypyridone ethylamine salt, difficult to guarantee product purity, long preparation process route and the like, To achieve the effect of simplifying the synthesis method process, safe and environmentally friendly reaction conditions, and reducing production costs

Pending Publication Date: 2021-11-05
CHENGDU ORGANOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem to be solved by the present invention is that the existing process route for preparing oxypirox ethylamine salt is long, the yield is low, the product purity is difficult to guarantee, and the environmental pollution is large. The purpose is to provide a kind of oxypirox ethylamine salt. The synthesis method solves the problems of long preparation process route, low yield, difficulty in guaranteeing product purity, and large environmental pollution

Method used

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  • Synthesis method of hydroxypiperidinone ethylamine salt
  • Synthesis method of hydroxypiperidinone ethylamine salt
  • Synthesis method of hydroxypiperidinone ethylamine salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] S1: 3,7,9,9-Tetramethyl-2-decene-5-oxoic acid methyl ester (intermediate M1) Preparation:

[0039] Add dichloroethane (25ml), isononanoyl chloride (9.23g, 52.6mmol, 1.2eq), iron trichloride (8.53g, 52.6mmol, 1.2eq) successively in the three-necked flask, after stirring at room temperature for 30min, add 3 , 3-methyl methacrylate (5.0g, 43.8mmol, 1.0eq), after the addition was complete, the system was refluxed at an external temperature of 40°C and an internal temperature of 37°C, and the reaction was completed by HPLC detection. Pour the reaction system into a mixed solution of ice water (40ml) and hydrochloric acid (2.0ml), stir and separate layers, wash the organic phase with water, wash with saturated aqueous sodium bicarbonate solution, dry over anhydrous sodium sulfate, and concentrate the organic phase to obtain 10.0g The intermediate M1 of reddish-brown oil has a yield of 89.77% and a purity of 96.7% by HPLC.

[0040] S2: Oxypiroxone (Intermediate M2) Crude Prepar...

Embodiment 2

[0048] S1: Preparation of methyl 3,7,9,9-tetramethyl-2-decene-5-ketoate (intermediate M1):

[0049] Add 1,2-dichloroethane (25ml), isononanoyl chloride (9.23g, 52.6mmol, 1.2eq), anhydrous tin tetrachloride (11.41g, 43.8mmol, 1.0eq) successively in a three-necked flask, room temperature After stirring for 30 minutes, 3,3-methyl methacrylate (5.0 g, 43.8 mmol, 1.0 eq) was added. After the addition was complete, the system was refluxed at an external temperature of 84°C and an internal temperature of 80°C, and the reaction was completed by HPLC detection. Pour the reaction system into a mixed solution of ice water (40ml) and hydrochloric acid (2.0ml), stir and separate layers, wash the organic phase with water, wash with saturated aqueous sodium bicarbonate, dry over anhydrous sodium sulfate, collect and concentrate the organic phase. phase, 9.26g of intermediate M1 of reddish-brown oil was obtained, with a yield of 83.11% and a purity of 97.5%.

[0050] S2: Preparation of Oxypi...

Embodiment 3

[0055] S1: Preparation of methyl 3,7,9,9-tetramethyl-2-decene-5-ketoate (intermediate M1):

[0056] Add dichloromethane (125ml) and isononanoyl chloride (46.15g, 0.26mol, 1.2eq) successively into a three-necked flask, cool down to -9°C, and then add aluminum trichloride (73.00g, 0.55 mol, 2.5eq), after stirring at room temperature for 30min, add 3,3-methyl methacrylate (25.0g, 0.22mol, 1.0eq), after the addition, the system is at an external temperature of 40°C and an internal temperature of 37°C Carry out reflux reaction, detect reaction progress by HPLC, treat that reaction finishes, and reaction system is poured in the ice water (200ml), stirs layering, and organic phase is washed with the hydrochloric acid solution of 1mol / L, then washes once with purified water, washes with free Dry over sodium sulfate and concentrate the organic phase to obtain 52.60 g of dark green oily intermediate M1 with a yield of 94.42% and a HPLC purity of 97.2%.

[0057] S2: Oxypiroxone (Interme...

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Abstract

The invention discloses a synthesis method of hydroxypiperidone ethylamine salt, which comprises the following steps of: S1, adding isononanoyl chloride, Lewis acid and methyl 3,3-dimethylacrylate into a container, and carrying out a Friedel-Crafts acylation reaction to obtain an intermediate M1; S2, adding the intermediate M1 and hydroxylamine hydrochloride into a solvent, and carrying out ring closing and hydroxyamination reactions at 0-140 DEG C to obtain an intermediate M2; and S3, carrying out a salt forming reaction on the intermediate M2 and ethanolamine to obtain hydroxypiperidinone ethylamine salt. According to the invention, the ring closing reaction and the hydroxyamination reactions can be achieved only in one reaction system to obtain hydroxypicolinone, such that the process of the hydroxypicolinone ethylamine salt synthesis method is simplified compared with the existing two reaction systems for carrying out ring closing to obtain lactone and then carrying out hydroxyamination to obtain hydroxypicolinone. The reaction system is low in temperature, low in requirements on process and equipment, safe in reaction condition, simple and convenient to operate and suitable for industrial mass production; and concentrated sulfuric acid, acetic acid, alkali and a catalyst are not needed, safety and environmental protection are achieved, and cost is reduced.

Description

technical field [0001] The invention relates to the technical field of synthesis of oxypirox ketamine salt, in particular to a synthesis method of oxypirox ketamine salt. Background technique [0002] Oxypiroxetine salt has excellent antipruritic effect, unique effect on eliminating skin itching, can effectively kill fungi that grow on the skin, and has special effect of removing body odor, good compounding property, safe, non-toxic, Non-irritating, it is an ideal high-efficiency fungicide, mainly used in shampoo, hair care, body wash, cosmetics, skin care products, and washing products. [0003] At present, the current reported process basically adopts the Friedel-Crafts reaction of methyl acrylate and isononanoyl chloride to obtain 3,7,9,9-tetramethyl-2-decene-5-keto acid methyl ester, and the ring closure reaction of methyl ester to obtain 4 -M-(2,4,4-trimethylpentyl)-2H-pyran-2-one, pyrone hydroxylamine hydrolysis to obtain oxypirone, and then salt-forming reaction with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/89C07C213/08C07C215/08C07C67/347C07C69/738
CPCC07D213/89C07C213/08C07C67/347C07C215/08C07C69/738
Inventor 王利民谈平忠邓倩郑守军
Owner CHENGDU ORGANOCHEM CO LTD