Synthetic method for codamine

The technology of a condensing agent and an intermediate is applied in the field of preparing ketamine, which can solve problems such as high separation difficulty, and achieve the effects of high separation difficulty, high identification difficulty and short reaction time.

Inactive Publication Date: 2014-08-06
公安部禁毒情报技术中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the main disadvantage of this method is that eight isomers are obtained, which are very difficult to separate

Method used

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  • Synthetic method for codamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 196 mg of 3,4-dimethoxyphenylacetic acid (purchased from Bailingwei Technology Co., Ltd.) and 245 mg of 4-hydroxy, 3-methoxyphenethylamine hydrochloride (purchased from Matrix Scientifi) and 569 mg HBTU (purchased from Bailingwei Technology Co., Ltd.) was added to 3 mL of pyridine, and then stirred at room temperature for 6 hours. Add 10 mL of ethyl acetate, wash with ammonium chloride aqueous solution and NaCl aqueous solution for 2-3 times to extract, and obtain the organic phase; dry the organic phase with anhydrous sodium sulfate, spin off the ethyl acetate to obtain intermediate I ( 350 mg, crude product, LCMS purity 92%)). Carry out NMR test to intermediate I, 1 H NMR (300 MHz, CDCl 3 ) δ 6.77 (dd, J = 8.3, 4.9 Hz, 2H), 6.69-6.64 (m, 2H), 6.58 (d, J = 1.9 Hz, 1H), 6.49 (dd, J = 8.0, 1.9 Hz, 1H) , 3.88 (s, 3H), 3.83 (d, J = 1.3 Hz, 6H), 3.46 – 3.38 (t, J = 6.9 Hz, 2H), 2.80 (s, 2H), 2.66 (t, J = 6.9 Hz, 2H). ESI 346 (M+1) + .

[0030] Add 350 mg of Intermedia...

Embodiment 2

[0033] 196 mg of 3,4-dimethoxyphenylacetic acid (purchased from Bailingwei Technology Co., Ltd.) and 225 mg of 4-hydroxy, 3-methoxyphenethylamine hydrochloride (purchased from Matrix Scientifi) 493 mg of HBTU (purchased from Bailingwei Technology Co., Ltd.) was added to 3 mL of pyridine, and then stirred at room temperature for 3 hours. Add 10 mL of ethyl acetate, wash with ammonium chloride aqueous solution and NaCl aqueous solution for 2-3 times, the organic phase is dried with anhydrous sodium sulfate, spin off ethyl acetate to obtain intermediate I (340 mg, crude product, LCMS purity 90 %).

[0034] Add 340mg of intermediate I to 3mL of toluene, then add 0.8 mL of phosphorus oxychloride to obtain a reaction solution; heat the reaction solution to 110°C and stir for 2 hours, then cool it, spin off toluene and excess phosphorus oxychloride , add a little ice-water mixture, adjust the pH value to 8-9 with sodium carbonate aqueous solution, then extract 2-3 times with 10 mL o...

Embodiment 3

[0037] 196 mg of 3,4-dimethoxyphenylacetic acid (purchased from Bailingwei Technology Co., Ltd.) and 205 mg of 4-hydroxy, 3-methoxyphenethylamine hydrochloride (purchased from Matrix Scientifi) and 455 mg of HBTU (purchased from Bailingwei Technology Co., Ltd.) was added to 3 mL of pyridine, and then stirred at room temperature for 3 hours. Add 10 mL of ethyl acetate, wash with ammonium chloride aqueous solution and NaCl aqueous solution 2-3 times, the organic phase is dried with anhydrous sodium sulfate, spin off ethyl acetate to obtain intermediate I (345 mg, crude product, LCMS purity 91%), directly used in the second step reaction.

[0038] Add 345mg of intermediate I to 3mL of toluene, and then add 0.5mL of phosphorus oxychloride to obtain a reaction solution; the reaction solution is heated to 110°C and stirred for 2 hours, then cooled, and the toluene and excess phosphorus oxychloride are removed by rotation. Add a little ice-water mixture, adjust the pH value to 8-9 w...

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Abstract

The invention provides a chemical synthetic method for codamine. According to the method, 3,4-dimethoxy phenylacetic acid and 4-hydroxy-3-methoxy phenylethylamine hydrochloride are used as starting raw materials, three steps of reactions consisting of acid amide condensation for preparation of an intermediate I, dehydration with phosphorous oxychloride for preparation of an intermediate II and reduction of the intermediate II are carried out to prepare codamine, and overall yield is 34%. The method provided by the invention has the characteristics of simple operation, easy availability of raw materials, short reaction time, etc.

Description

technical field [0001] The invention relates to a method for preparing codanmine. Background technique [0002] In recent years, the drug problem has become increasingly serious around the world, causing great harm to society. Heroin is one of the most common types of drugs. Opium (Papaver somniferum) is the starting material for the preparation of heroin. Opium contains a variety of constant and trace alkaloids. These alkaloids are one of the main means to distinguish opium samples from different regions . [0003] Codamine and laudanine are important trace alkaloids in opium, and their molecular formulas are C 20 h 25 NO 4 , it is difficult to determine the retention time of two compounds on liquid chromatography in the absence of reference substances or standards. At present, it is difficult to buy the reference or standard substance of codanline in the market, so the synthesis of codanline is of great significance for determining its retention time on the liquid pha...

Claims

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Application Information

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IPC IPC(8): C07D217/20
CPCC07D217/20
Inventor 刘翠梅白燕平
Owner 公安部禁毒情报技术中心
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