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Novel process for preparing ractopamine from p-hydroxyacetophenone and raspberry ketone

A technology of p-hydroxyacetophenone and ractopamine, which is applied in the field of preparation of organic compounds, can solve the problems of low yield of N-alkylation reaction, high market price, and influence on yield, and achieves less by-products and better synthesis Simple steps and good quality results

Inactive Publication Date: 2004-12-29
QINGYUAN HUACHEN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the N-alkylation reaction yield in the third step of the patent reaction process is low (20-28%), which affects the yield of the entire reaction, and uses tetrahydrofuran (THF) as a solvent, and the market price is relatively expensive

Method used

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  • Novel process for preparing ractopamine from p-hydroxyacetophenone and raspberry ketone
  • Novel process for preparing ractopamine from p-hydroxyacetophenone and raspberry ketone
  • Novel process for preparing ractopamine from p-hydroxyacetophenone and raspberry ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 300 milliliters of carbon tetrachloride, 25.0 grams of p-hydroxyacetophenone in a 500 milliliter four-neck round bottom reaction flask with magnetic stirring, reflux condenser, chlorine conduit and thermometer, heat to reflux (temperature is 85 ℃), pass Chlorine gas was added to react, and the end point was determined by spotting on a thin-layer chromatographic plate. After the reaction, cool down, add sodium bicarbonate to neutralize, filter, concentrate and crystallize the filtrate, and obtain white crystals after drying.

[0038] Yield: 25.1 Yield: 85%

[0039] Melting point: 130-132°C

[0040] Elemental Analysis: C 8 h 7 o 2 CL M.W.: 170.6

[0041] Theoretical value: C56.32 H4.14 Cl20.78

[0042] Analytical value: C56.09 H4.06 Cl21.12

Embodiment 2

[0044] Add 100 milliliters of 10% sodium carbonate aqueous solution, 100 milliliters of ethyl acetate, 8.2 grams (50 mmol) of 1-methyl-3-(4-hydroxyphenyl)-propylamine and 10.0 g (60 mmol) of -chloro-p-hydroxyacetophenone, stirred vigorously at room temperature. In the first few minutes, all the reactants were dissolved into a brownish-red solution. After about one hour, a large amount of white precipitates began to be produced, and the reaction was completed after about 4 hours.

[0045] Filter with suction, wash with ethyl acetate and distilled water three times each, and drain.

[0046] Transfer the filter cake into a 500ml flask, add 100ml of water, add concentrated hydrochloric acid dropwise until pH = 2, heat to reflux, stir to acidify, and cool to crystallize.

[0047] Yield: 6.0 g Yield: 40.8%

[0048] Melting point: 105-107°C

[0049] Elemental Analysis: C 18 h 22 o 3 CL M.W.: 335.8

[0050] Theoretical value: C64.37 H6.60 N4.17 Cl10.56

[0051] Analytical value:...

Embodiment 3

[0053] Add 30.0 grams (90 mmol) of the white powdery product obtained in Example 2 in a 1000 milliliter hydrogenation reactor, 3.0 grams of Raney nickel, 500 milliliters of absolute ethanol, and hydrogenate at 8Mpa at 140°C until no hydrogen is absorbed.

[0054] After the hydrogenation is completed, filter, and the filtrate is distilled under reduced pressure to remove ethanol, and dried to obtain a light yellow solid product, which is Ractopamine Hydrochlide.

[0055] Melting point: 137-139°C

[0056] Yield: 29.7 g Yield: 99%

[0057] Elemental Analysis: C 18 h 23 o 3 CL M.W.: 337.83

[0058] Theoretical value: C63.99 H7.16 N4.15 Cl10.49

[0059] Analytical value: C63.69 H7.03 N4.08 Cl10.36

[0060] (The results of product mass spectrometry are shown in the attached figure 1 :)

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Abstract

The present invention is the new preparation process of Ractopamine with p-hydroxyacetophenone and raspberry ketone. The Ractopamine product has simple production process, high quality, cheap material and high yield, and is suitable for industrial production.

Description

1. Technical field [0001] The invention discloses a preparation method of an organic compound, and more particularly discloses a new method for preparing Ractopamine Hydrochloride from p-hydroxyacetophenone and raspberry ketone. 2. Background technology [0002] Ractopamine belongs to phenylethanolamine compounds and also belongs to β-adrenaline compounds. These compounds have extremely high physiological activity and medicinal value, and play an important role in regulating the physiological process of energy metabolism in animals. Its chemical synthesis Methods and areas of application have always been valued by people. [0003] The scientific name of Ractopamine Hydrochloride is: 4-hydroxy-α-[[[3-(4-hydroxyphenyl)-1-methylpropyl]amino]methyl]-benzyl alcohol-hydrochloride {4-Hydroxy-α -[[[3-(4-Hydroxyphenyl)-1-Methylpropyl]amino]methyl]-Benzenemethnol}, its chemical structural formula is: [0004] [0005] Ractopamine Hydrochloride is a new type of feed additive succe...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C215/60
Inventor 胡厚才
Owner QINGYUAN HUACHEN IND
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