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Method for preparing amino ether compounds

A technology for amino ethers and compounds, which is applied in the field of preparation of amino ether compounds, can solve the problems of high price, cumbersome post-processing, poor selectivity and the like, and achieves the effects of low production cost, wide application range and good yield.

Inactive Publication Date: 2017-05-10
PAPANNA BEIJING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In summary, the existing amino alcohol synthesis method mainly has the following defects: (1) use expensive alkali; (2) the alkali used has strong corrosiveness or reducibility, and the process operation reaction is violent, and the reaction is not easy Control, very dangerous, is unfavorable for industrialized production; (3) reaction condition requirement is higher, needs anhydrous operation, aftertreatment is loaded down with trivial details, is unfavorable for industrialized production; (4) the productive rate of reaction is relatively low; (5) the selectivity of reaction is poor

Method used

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  • Method for preparing amino ether compounds
  • Method for preparing amino ether compounds
  • Method for preparing amino ether compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: the preparation of 3-amino-1-propyl methyl ether

[0057] (1) Add benzaldehyde (1.00mol, 106g) to 300g cyclohexane solvent, add 3-amino-1-propanol (1.1mol, 82.50g), reflux at 90°C, add water divider to separate water, and react 3h, after the reaction was completed, the cyclohexane was distilled off to obtain 162.0 g of white crystalline solid A1 with a yield of 99.38% and a purity of 99.6%.

[0058] (2) 162.0gA1 is added in 500g toluene solvent, add 18-crown-6 phase transfer catalyst (6mmol, 1.62g, 0.6%), KOH (1.5mol, 84g), control reaction system temperature at -5~10 Between ℃, iodomethane (1.1mol, 157g) was added dropwise, the dropwise addition was completed in 2.5h, and the reaction was complete in 3.5h. Add 100 g of water, extract and separate the layers, wash the toluene layer once with 50 g of water, and then distill the toluene layer off to obtain 174 g of white solid B1; the yield is 99.43%, and the purity is 99.15%.

[0059] (3) Add 174g of B1 t...

Embodiment 2

[0061] Embodiment 2: the preparation of D-valline ether

[0062] (1) Add benzaldehyde (3.00mol, 318g) to 1000g toluene solvent, add D-valinol (3.3mol, 340.46g, ee value, 99.5%) to reflux, add water divider to remove water, and reflux for 4h After the reaction was completed, toluene was distilled off for post-treatment to obtain 568.30 g of white crystal A2 with a yield of 99.8% and a purity of 99.10%.

[0063] (2) 568.30gA2 is joined in 5000g tetrahydrofuran solvent, add 15-crown ether-5 phase-transfer catalyst (18mmol, 4g, 6%), NaOH (4.00mol, 160g) powder, control reaction system temperature at-5~10 Between ℃, (3.3mol, 416g) dimethyl sulfate was added dropwise, and the dropwise addition was completed within 4 hours. The cooling was removed to allow the reaction temperature to gradually rise to room temperature, and the reaction was carried out for 5 hours. After the reaction was completed, the solvent was removed, and the organic layer was washed with water to obtain 605.25...

Embodiment 3

[0066] Embodiment 3: L-amphetamine ether

[0067] (1) Benzaldehyde (1.10mol, 116g) was added to 500g xylene solvent, L-phenylalaninol (1.0mol, 151g, ee value, 99.8%) was added, and the water removal device was placed on top, and the reaction was refluxed for 4h, After the reaction was completed, xylene was distilled off under reduced pressure to obtain 237.00 g of white crystal A3 with a yield of 99.08% and a purity of 99.58%.

[0068] (2) 237gA3 is joined in 2400g n-hexane solvent, add TBAB (1mmol, 0.37g, 0.1%) phase transfer catalyst, NaOH (2.48mol, 99.08g), control reaction system temperature between-5~5 ℃, Benzyl chloride (1.19mol, 149.96g) was added dropwise, and the addition was completed within 1.5h. After 0.5 hours of reaction, the cooling was removed to allow the reaction temperature to gradually rise to room temperature, and the reaction was carried out for 3.5 hours. After the reaction was completed, 530 g of water was added, extracted and separated, and n-hexane ...

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Abstract

The invention belongs to the technical field of organic synthesis and relates to a method for preparing amino ether compounds. The method comprises the following steps: by taking amino alcohol as a raw material, protecting amino in the amino alcohol so as to obtain Schiff base; carrying out an etherification reaction on the hydroxyl group in the Schiff base; and finally, performing amino deprotection, thereby obtaining corresponding amino ethers. The method disclosed by the invention has high regio-selectivity, the substrates of higher than 99.9% are subjected to etherification reaction, the reaction conversion ratio of each step is higher than 99.8%, and the total yield is higher than 95%; when amino alcohol is chiral, the amino ethers with retention of configuration can be obtained; and moreover, each step of the method is a conventional operation, the process cost is low, and three wastes are few, the energy consumption is low, an environment-friendly effect is achieved, and large-scale industrial production is easily realized.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of amino ether compounds. Background technique [0002] Amino ether compounds have great medicinal value, such as diphenhydramine hydrochloride, doxylamine, carbinoxamine, stastatine, etc. are representative drugs with antihistamine activity. Amino ether compounds are also intermediates for the preparation of biologically active ingredients. (EP 0691346; T.Nishi et al. Chem.Pharm.Bull.1985,33(3), 1140-1147, D.Lewis et al. Steroids, 1995,60,475-483; D.Kikelj et al. J.Med.Chem. 1998, 41, 530-539; M.G.N.Russell et al. J.Med.Chem.1999, 42, 4981-5001; Fray et al. Bioorg.Med.Chem.Lett.2001, 11, 567-570; Koert et al. , 40(11), 2076-2078; Price et al. Tetrahedron Letters 2004, 45, 5581-5583). Amino ether compounds are also chiral auxiliary agents for chemical synthesis (T.K., Chakraborty etc. Tetrahedron 1995,51(33),9179-9190; Tetrahedron:Asymmetry 1998,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/08C07C217/44C07C217/48
CPCY02P20/582C07C213/02C07C249/02C07C217/08C07C217/44C07C217/48C07C251/08C07C251/16C07C251/18
Inventor 陈安军孙飞杨文龙徐格邹晨
Owner PAPANNA BEIJING TECH
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