Prochiral allyl amine compound and synthetic method thereof

A technology of allyl amine and synthesis method, which is applied in the field of synthesis of prochiral allyl amine compounds, can solve the problems of low yield, poor reaction selectivity, difficult procurement, etc., and achieve target yield and purity improvement, The effect of economical and easy access to raw materials

Active Publication Date: 2013-01-02
常州胜杰生命科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this response is that neryl chloride is expensive, and it is not easy to purchase and obtain, so it is not suitable for industrial production; according to the report, the preparation method of halodiamine is to use geranyl halide and diethylamine as raw materials. Catalyzed three-step reaction to get
The disadvantage of this method is that the reaction selectivity is poor and the yield is low

Method used

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  • Prochiral allyl amine compound and synthetic method thereof
  • Prochiral allyl amine compound and synthetic method thereof
  • Prochiral allyl amine compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Nerylamine, its structural formula is:

[0023]

[0024] The synthetic method of neroliamine comprises the steps:

[0025] In a dry 1-liter high-pressure reaction device, under the protection of nitrogen, add 340g of isoprene, 80g of diethylamine, 100ml of toluene, after stirring evenly, add 26ml of 2.5M n-hexane mixed solution of butyllithium, seal and Pressurize the kettle, control the reaction temperature at 70°C and the reaction pressure within the range of 80psi, react for 12 hours, after the reaction is completed, cool to room temperature, release the pressure and transfer the materials in the reactor to ice water, and separate the two phases at rest , the lower aqueous phase was extracted with methyl tert-butyl ether and incorporated into the organic phase, washed with saturated brine, dried over anhydrous sodium sulfate, and rectified. The obtained content is 99.0% of neroliamine, and the molar yield is 82%.

Embodiment 2

[0027] Nerylamine, its structural formula is:

[0028]

[0029] In a dry 1-liter high-pressure reaction device, under the protection of nitrogen, add 340g of isoprene, 80g of diethylamine, and 50ml of n-hexane. After stirring evenly, put 0.6g of pre-cut metal lithium particles into the kettle under stirring. Seal the device and pressurize the autoclave, control the reaction temperature within the range of 120°C and reaction pressure 140psi, and react for 24 hours. phase, the lower aqueous phase was extracted with ether and incorporated into the organic phase, washed with saturated brine, dried over anhydrous sodium sulfate, and rectified to obtain 176 g of nerylamine with a content of 99.5% and a molar yield of 90%.

Embodiment 3

[0031] Hazy bovine diamine, its structural formula is:

[0032]

[0033] In a dry 1-liter high-pressure reaction device, under the protection of nitrogen, add 136g of myrcene, 100g of diethylamine, and 200ml of cyclohexane. After stirring evenly, add 67ml of 1.5M tetrahydrofuran solution of butyllithium, and control the reaction temperature at Within the range of 65°C and reaction pressure 70psi, react for 4 hours, cool the reaction solution to room temperature, put it into ice water, and separate the two phases at rest. The lower aqueous phase is extracted with dichloromethane and incorporated into the organic phase, washed with saturated saline, Dried over sodium sulfate and rectified to obtain 97g of 99.3% oxadiamine, 25g of 96% oxadiamine, and 40g of 89% oxadiamine with a molar yield of 80%.

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PUM

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Abstract

The invention provides a prochiral allyl amine compound. The compound is neryl amine or (Z)-N, N-diethyl-3, 7-dimethyl-2, 6-octadiene-1-amine. A synthetic method of the prochiral allyl amine compound is provided. The method includes adding quantitative terpenoid compounds, diethylamine and solvents in a drying high pressure reaction device under the protection of inert atmosphere, uniformly stirring, adding quantitative catalysts, controlling the reaction temperature in a range from 50 DEG C to 150 DEG C and the reaction pressure in a range from 70psi to 140psi, reacting for 12 to 24 hours to obtain a reaction product, after the reacting is finished, cooling the reaction product to the room temperature, throwing the reaction product in ice water, keeping static to separate two phases, extracting the lower layer water phase by an extracting solvent, merging the extracted water phase into an organic phase, washing by saturated salt water, drying by anhydrous sodium sulfate, and distilling to obtain the required prochiral allyl amine compound.

Description

technical field [0001] The invention relates to a synthesis method of a precursor of a chiral drug, in particular to a synthesis method of a prochiral allylamine compound. Background technique [0002] Chiral allylamine compounds, especially (E)-N,N-diethyl-3,7-dimethyl-2,6-octadiene-1-amine or (Z)-N, N-diethyl-3,7-dimethyl-2,6-octadiene-1-amine, E)-N,N-diethyl-3,7-dimethyl-2,6-octyl Diene-1-amine, commonly known as nerylamine, (Z)-N,N-diethyl-3,7-dimethyl-2,6-octadien-1-amine, commonly known as hazy bovine diamine . [0003] Prochiral allyl amine compounds, especially nerylamine and oxadiamine, are important raw materials for the synthesis of flavors and flavors such as citral, citronellal, nerol, L-menthol and linalool. At the same time, it can also be used as the precursor of some chiral drugs to synthesize optically active drugs through asymmetric catalysis. According to reports, the synthetic method of nerylamine includes: reacting neryl chloride with diethylamine. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/21C07C209/60
Inventor 苏衡李海燕王加高申传伟
Owner 常州胜杰生命科技股份有限公司
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