Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride

A benzyl dimethyl and myristyl amide group technology is applied in the synthesis field of Mie's antibacterial drug propyl] ammonium chloride), which can solve the problem of high residual solvent control requirements, high reaction equipment requirements, and relatively high environmental impact. It can easily control the product quality, simplify the operation, and reduce the toxicity.

Inactive Publication Date: 2010-08-04
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Application Information

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Problems solved by technology

The weak point of this method is: (1) adopt the bigger benzene of toxicity as solvent, bigger impact on environment, and the control requirement of residual solvent in the product is higher; (2) involve 10% hydrogen in the synthesis of intermediate Sodium oxide solution and water washing, the nature of intermediate makes easy to produce emulsification phenomenon in the processing process, inconvenient to operate; (3) 3-myristyl amido-N, N-dimethylpropylamine is solid, and its boiling point is higher (208 -215℃ / 1-2mmHg), it needs to be obtained by vacuum distillation under high vacuum, which requires high reaction equipment

Method used

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  • Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride
  • Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride
  • Method for synthesizing benzyldimethyl[3-(myristamide)propyl]ammonium chloride

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Embodiment 1

[0025] (1) Add N,N-dimethylpropylenediamine (31.0g, 0.303mol), 600ml ethyl acetate and triethylamine (31.0g, 0.306mol) to a 1000ml round bottom bottle, and add dropwise under stirring Myristoyl chloride (73.8 g, 0.299 mol). After the addition was complete, the reaction was heated to reflux for 3 hours and cooled to room temperature. The precipitated white solid was filtered off, and ethyl acetate was concentrated under reduced pressure to dryness to obtain a white solid. Add 250ml of petroleum ether at 60-90°C for recrystallization to obtain 72.2g of 3-myristoylamino-N,N-dimethylpropylamine as a white solid with a yield of 77.4% based on myristoyl chloride and a melting point of 51-52°C .

[0026] 1 H NMR (CDCl 3 )δ: 0.88(t, 3H), 1.28(m, 20H), 1.63(m, 4H), 2.14(t, 2H), 2.23(s, 6H), 2.37(t, 2H), 3.34(q, 2H ), 6.94 (br, 1H).

[0027] (2) Add 3-myristamido-N, N-dimethylpropylamine (62.4g, 0.20mol, 750ml ethyl acetate to a 2000ml round bottom bottle, add benzyl chloride (34....

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Abstract

Synthesis of benzyl-methyl(3-(myristoyl amino)propyl)ammonia chloride adopts organic acid ester as reactive solvent. It's convenient and non-toxic.

Description

technical field [0001] The invention relates to a synthesis method of Myramistin antibacterial drug (myramistin, myramistin, whose chemical name is: benzyl dimethyl [3-(myristyl amido) propyl] ammonium chloride). Background technique [0002] Myramistin is a surfactant broad-spectrum bactericidal drug developed in Russia. It has an antibacterial effect on Gram-positive bacteria and Gram-negative bacteria, aerobic bacteria and anaerobic bacteria, spore-producing and non-spore-producing bacteria; it has antibacterial effects on venereal pathogens (chlamydia, vaginal trichomonas, gonorrhea, etc.), herpes viruses and Immunodeficiency also has a therapeutic effect, and is widely used in the fields of surgery and trauma, obstetrics and gynecology, burns, dermatology and venereal diseases. [0003] The structure of Myramistin (myramistin) is as follows: [0004] [0005] Its synthetic method has been reported, and US2459062 discloses that N, N-dimethylpropylenediamine and myri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C219/22A61K31/16A61P31/04
Inventor 丁日高张城王好山钟玉绪全东琴应翔宇恽榴红林京玉徐贵霞李博
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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