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Preparation method of 4-methoxy-beta-phenylethylamine

A technology of methoxybenzaldehyde and methoxy, which is applied in the field of preparation of 4-methoxy-β-phenethylamine, can solve the problems of cumbersome reaction steps, low reaction yield, difficult industrialization and the like, and achieves reactivity High, simple operation steps, short response time effect

Inactive Publication Date: 2013-03-20
张家港市大伟助剂有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the technology used in industrial production has the disadvantages of high cost of raw materials, low reaction yield, cumbersome reaction steps, and difficulty in industrialization.

Method used

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  • Preparation method of 4-methoxy-beta-phenylethylamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1) Preparation of 4-methoxy-β-nitrostyrene

[0018] In the reactor, add 20.4g (0.15mol) 4-methoxybenzaldehyde, 20.1g (0.33mol) nitromethane, 14.0g (0.18mol) ammonium acetate and 75ml (1.3mol) glacial acetic acid, stir and heat to reflux, After reacting for 4~4.5h, the reaction solution was cooled to 12~15°C, then poured into ice water at -2~2°C, yellow needle-like crystals were precipitated, filtered with suction, the filter cake was washed with water, and dried to obtain 4-methoxy- β-nitrostyrene is a yellow solid, and then recrystallized with tetrahydrofuran alcohol to obtain 23.5 g of yellow crystals, yield: 87.3%, m.p.: 85~87 °C;

[0019] 2) Preparation of 4-methoxy-β-phenethylammonium

[0020] Add 64.9g (1.0mol) of zinc powder into the reaction, then add 10~30Wt.% hydrochloric acid aqueous solution, the amount added is less than the zinc powder, stir evenly, let stand for 0.5~1h, filter to obtain activated zinc powder;

[0021] In the reactor, add activated zinc ...

Embodiment 2

[0023] 1) Preparation of 4-methoxy-β-nitrostyrene

[0024] In the reactor, add 20.4g (0.15mol) 4-methoxybenzaldehyde, 24.7g (0.45mol) nitromethane, 16.4g (0.21mol) ammonium acetate and 82ml (1.4mol) glacial acetic acid, stir and heat to reflux, After reacting for 4~4.5h, the reaction solution was cooled to 10~15°C, then poured into ice water at -2~2°C, yellow needle-like crystals were precipitated, filtered with suction, the filter cake was washed with water, and dried to obtain 4-methoxy- β-Nitrostyrene is a yellow solid, and then recrystallized from tetrahydrofuran alcohol to obtain 23.8g of yellow crystals, yield: 88.5%, m.p.: 85~87°C;

[0025] 2) Preparation of 4-methoxy-β-phenethylammonium

[0026] Add 54.5g (0.84mol) of zinc powder into the reaction, then add 10~30Wt.% hydrochloric acid aqueous solution, the amount added is less than the zinc powder, stir evenly, let stand for 1h, and filter to obtain activated zinc powder;

[0027] In the reactor, add activated zinc p...

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Abstract

The invention discloses a preparation method of 4-methoxy-beta-phenylethylamine. The method comprises the following preparation steps: 1) reacting 4-methoxy benzaldehyde, nitromethane, ammonium acetate and glacial acetic acid to obtain 4-methoxy-beta-nitrostyrolene; and 2) stirring and reacting activated zinc powder, 4-methoxy-beta-nitrostyrolene and 30-32wt% of hydrochloric acid aqueous solution, distilling under reduced pressure after post-treatment to obtain 4-methoxy-beta-phenylethylamine. The method disclosed by the invention has the advantages of simple operation steps, low cost of the reducing agent, high reaction activity due to Zn powder activated by hydrochloric acid, short reaction time and high yield. The sodium bicarbonate solution is used for neutralizing in the post-treatment after the reduction reaction is ended and then 4-methoxy-beta-phenylethylamine is obtained.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 4-methoxy-β-phenethylamine. Background technique [0002] The β-phenylethylamine compounds with methoxyl or hydroxyl groups on the benzene ring are commonly used intermediates in the synthesis of drugs, which can be obtained by reducing the corresponding phenylacetonitrile or nitrostyrene. [0003] At present, the technology used in industrial production has the disadvantages of high raw material cost, low reaction yield, cumbersome reaction steps, and difficulty in industrialization. Contents of the invention [0004] The technical problem to be solved by the present invention is to provide a method for preparing 4-methoxy-β-phenylethylamine with low raw material cost, mild reaction conditions, high reaction yield and easy industrialization. [0005] In order to solve the problems of the technologies described above, the technical solution ...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C215/52
Inventor 龚卫良黄德周
Owner 张家港市大伟助剂有限公司
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