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Preparation of 10,11-dihydrodibenzo[b,f] cyproheptadine-10-ketone compound

A technology of ketone compounds and borohydride compounds, applied in organic chemistry and other directions, can solve the problems of many reaction steps, "three wastes" and low total yield, and achieve the effects of mild reaction conditions, less pollution of "three wastes" and easy operation.

Inactive Publication Date: 2007-06-06
SICHUAN UNIV
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Problems solved by technology

[0009] There are many deficiencies in the above two methods: the price of raw materials used in method one is higher; the "three wastes" are serious in the preparation process, such as: intermediate (II) is converted into phenylacetic acid through Willgerodt rearrangement In the process, more toxic sulfur will be used, and highly toxic hydrogen sulfide gas will be produced in the hydrolysis process after rearrangement; due to the low conversion rate of Willgerodt rearrangement, the total yield of the process is low, etc.
There are many reaction steps in method two, resulting in lower overall yield; the raw materials used in the preparation are not easy to get (such as: 2-iodobenzoic acid), expensive (such as: lithium aluminum hydride), and also use highly toxic cyanide Chemicals; the "three wastes" are serious in the preparation process; the reaction operation and post-treatment process are cumbersome and other deficiencies

Method used

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  • Preparation of 10,11-dihydrodibenzo[b,f] cyproheptadine-10-ketone compound
  • Preparation of 10,11-dihydrodibenzo[b,f] cyproheptadine-10-ketone compound
  • Preparation of 10,11-dihydrodibenzo[b,f] cyproheptadine-10-ketone compound

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Experimental program
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Effect test

Embodiment 1

[0029] 27.2g (0.15mol) of o-nitrophenylacetic acid and 100ml of isopropanol were added to the hydrogenation reaction kettle, after stirring at room temperature until the solid was completely dissolved, 2.7g of Raney Ni catalyst was added, and the reaction kettle was replaced with hydrogen three times at 50° C., 1.0×10 6 The reaction was maintained and stirred under Pa pressure for 2 hours. After the reaction was completed, it was cooled to room temperature, filtered, and a small amount of isopropanol was used to wash the filter cake. After the filtrate and the washings were combined, the solvent was recovered under reduced pressure, cooled and dried to obtain 22.2 g of white powder solid (II), mp 118~119 ° C, collected. rate 98.0%.

Embodiment 2

[0031] Mix 36.2 g (0.2 mol) of o-nitrophenylacetic acid, 19.8 g (0.2 mol) of anhydrous cuprous chloride and 200 ml of methanol, stir at room temperature for 10 minutes, and add KBH in batches 4 21.6 g (0.4 mol), then the reaction was stirred at room temperature for 1 hour. After the reaction, methanol was evaporated under reduced pressure, 150 ml of deionized water was added to the residue, the pH of the solution was adjusted to 3-4 with 4 mol / L HCl aqueous solution, the obtained solution was extracted with ethyl acetate 60 mL×3, and the extract was recovered under reduced pressure. , cooled and dried to obtain a white powder solid (II) 28.7g, mp117~119℃, yield 95.0%.

[0032] Two. the preparation of o-diazophenylacetic acid (III)

[0033] Example 1

[0034] Add 30.2 g (0.2 mol) of o-aminophenylacetic acid, 160 ml of deionized water and 43 ml of concentrated HCl into the reaction flask, stir until the solid is completely dissolved, after the solution is cooled to 0 °C, slow...

Embodiment 3

[0043] Add 32.0 g (0.8 mol) of sodium hydroxide and 200 ml of deionized water to the reaction flask, stir until the solid is completely dissolved, and after cooling to 0 °C, add 29.4 g (0.21 mol) of 4-methoxythiophenol and freshly prepared 2.5 g of Cu powder, after stirring evenly, slowly add the o-diazophenylacetic acid (III) hydrochloride aqueous solution prepared in the previous step dropwise, control the dropping rate, and maintain the temperature of the reaction solution at 0-5 °C, about 1.5 The dripping was completed in an hour; after the reaction solution was kept at 0-5° C. for 1.5 hours and stirred for reaction, the temperature was raised to room temperature, and the stirring reaction was continued for 10 hours. After the reaction is completed, filter, wash the filter cake with a small amount of deionized water, combine the filtrate and the washing solution, neutralize the pH of the solution to 2-3 with concentrated hydrochloric acid, extract with 80 mL × 3 of ethyl ac...

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Abstract

Production of 10,11-dihydro-dibenzo(b, f)chedder-10-ketone compound is carried out by taking o-nitrophenylacetic acid as initial raw material, reducing, diazotizing, coupling with phenyl-sulfhydrate derivatives, acylating, and cyclizing to obtain (I). It achieves simple process, gentle reaction and more yields.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new method for preparing a medicinal intermediate 10,11-dihydro-dibenzo[b,f]cyptain-10-one compound (I). [0002] [0003] (wherein R represents H, halogen, alkyl, alkoxy, alkylthio, amide) Background technique [0004] 10,11-Dihydro-dibenzo[b,f] cypressin-10-one compound (I) is a synthetic non-steroidal anti-inflammatory drug Zaltoprofen (Zaltoprofen), antipsychotic drug zotepine (Zotepine) and other important intermediates of drugs. Foreign literature: Monatsh Chem 1965, 96, 182; Chem Pharm Bull 1975, 23, 2223; Chem Pharm Bull 1978, 26, 3058; Pharmaceutical Journal (Japan) 1968, 88, 1323; Chem Ber 1981, 114, 2382; domestic literature : West China Journal of Pharmacy 2003, 18, 118; describes the preparation methods of these compounds, these methods can be divided into the following two methods according to the different starting materials used, and the reaction formula is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D337/14
Inventor 邓勇沈怡钟裕国杨宇严忠勤
Owner SICHUAN UNIV
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