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A kind of synthetic method of methoxyphenamine hydrochloride

A technology of methoxyphenamine hydrochloride and methoxybenzene, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino hydroxyl compounds, etc., can solve problems such as unfavorable industrial production, difficult separation and purification, and large amount of manganese acetate , to achieve the effects of less three wastes, high reaction yield and low raw material cost

Inactive Publication Date: 2011-12-07
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is a competitive reaction in this method, the ratio of o-, m-, p- is 84:2:13, separation and purification are difficult, and the amount of manganese acetate is large, and a large amount of waste residue will be produced after the reaction, which is not easy to handle
[0008] About the preparation method of intermediate o-methoxy amphetamine, Journal of Chromatographic Science, 1989,27 (10), 602-6 has reported that with o-methoxy propiophenone, methylamine is raw material, with cyanoborohydrogenation Sodium is reduced to obtain o-methoxyamphetamine, and the price of sodium cyanoborohydride reducing agent used in the reaction is relatively expensive, which is not conducive to industrial production

Method used

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  • A kind of synthetic method of methoxyphenamine hydrochloride
  • A kind of synthetic method of methoxyphenamine hydrochloride
  • A kind of synthetic method of methoxyphenamine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of o-methoxypropiophenone (III)

[0033] In a 1L three-necked flask, add 367g of acetic anhydride, 300g of o-methoxyphenylacetic acid, and 100g of pyridine in sequence, react at 40°C for 6 hours under nitrogen protection, remove excess anhydride under reduced pressure, add 400mL of 20% NaOH, stir, and then add Extract with 400mL of dichloromethane, wash the separated organic layer with 150mL of dilute hydrochloric acid and 200mL of pure water to remove pyridine, recover the dichloromethane under reduced pressure, distill the residue under reduced pressure, collect the fraction at 90-100℃ / 5mmHg, and obtain 197.3g O-methoxypropiophenone, yield 75%, GC purity 99.3%.

Embodiment 2

[0034] Embodiment 2: the preparation of o-methoxypropiophenone (III)

[0035] The mass ratio of the feed is o-methoxyphenylacetic acid: acetic anhydride: N-methylimidazole=1:0.5:0.4, the reaction temperature is 80°C, the reaction time is 5h, the organic solvent A is ethyl acetate, and the mass dosage is o-methoxyphenylacetic acid 2 times the quality of oxyphenylacetic acid, other operations are the same as in Example 1; the product o-methoxypropiophenone is obtained with a yield of 79.5% and a GC purity of 99.2%.

Embodiment 3

[0036] Embodiment 3: the preparation of o-methoxypropiophenone (III)

[0037]The mass ratio of the feed is o-methoxyphenylacetic acid: acetic anhydride: quinoline=1:1:0.6, the reaction temperature is 160°C, the reaction time is 1h, the organic solvent A is chloroform, and the mass dosage is the quality of o-methoxyphenylacetic acid 3 times, other operation is the same as embodiment 1; Obtain product o-methoxy Propiophenone, yield 72.5%, GC purity 98.9%.

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Abstract

The invention provides a method for synthesizing methoxyphenamine hydrochloride. The method comprises the following steps of: (1) mixing o-methoxyphenylacetic acid with organic alkali, dissolving in acetic anhydride for undergoing a heating reaction, and performing post-treatment to obtain o-methoxybenzyl methyl ketone; (2) putting the o-methoxybenzyl methyl ketone and a methylamine alcohol solution into a high-pressure kettle for performing catalytic hydrogenation to obtain o-methoxy phenpromethamine; and (3) introducing dried HCl gas into a solution containing o-methoxy phenpromethamine forsalifying, and recrystallizing the obtained crude product to obtain methoxyphenamine hydrochloride. The method has the advantages of easiness and convenience for operation, mild reaction condition, high reaction yield, small quantity of three wastes, lower raw material cost, easiness for industrialization, and the like.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing methoxyphenamine hydrochloride. (2) Background technology [0002] Methoxyphenamine hydrochloride, also known as methamphetamine hydrochloride, is a type of β-adrenergic receptor agonist, mainly stimulating β receptors, and has a very weak effect on α receptors, and its antiasthmatic effect is stronger than that of ephedrine , less cardiovascular system side effects, clinically mainly used for bronchial asthma, especially those who cannot tolerate ephedrine. Its structural formula is as follows: [0003] [0004] At present, the price of methoxyphenamine hydrochloride bulk drug in the Chinese market is more expensive, and the traditional method for preparing methoxyphenamine hydrochloride is J.Am.Chem.Soc., 1953,75 (4), reported in 921-915 O-methoxybenzaldehyde is used as the starting material, condensed with nitroethane under alkaline conditions, and then reduced by iron / ferric chloride / hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/60C07C213/02
CPCY02P20/584
Inventor 钟为慧姚奕施湘君苏为科李智林谈伟平
Owner ZHEJIANG UNIV OF TECH
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