Synthesis method of loxoprofen sodium

A technique for loxoprofen sodium and a synthetic method, which is applied in the chemical industry, can solve problems such as high cost and low yield, and achieve the effects of low production cost, increased product yield, and reduced reaction steps

Inactive Publication Date: 2019-05-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The current technique of producing loxoprofen sodium has the disadvantages of high cost and low yield

Method used

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  • Synthesis method of loxoprofen sodium
  • Synthesis method of loxoprofen sodium
  • Synthesis method of loxoprofen sodium

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Experimental program
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Embodiment 1

[0050] The synthetic method of embodiment 1, loxoprofen sodium, carries out following steps successively:

[0051] 1), condensation reaction prepares N-(1-cyclopentenyl) morpholine:

[0052] Take 16.8g (0.2mol, 18ml) of cyclopentanone and 52.3g (0.6mol) of morpholine into a 250mL three-neck flask, add 0.2g of p-toluenesulfonic acid, 100mL of toluene, heat to reflux (about 110°C), and azeotrope With water, remove the water generated by the reaction from the reaction system in real time to promote the reaction. After 8 hours of reaction, 3.4g of water is brought out; at this time, no more water is taken out; the resulting reaction solution is distilled at atmospheric pressure (110-130°C) , Collect about 116.6g of the preceding cut, then vacuum distillation, collect the cut (20mmHg) of 108~115 ℃, obtain product N-(1-cyclopentenyl) morpholine 27.3g, yield is 89.3%.

[0053] The main components of the former fraction are toluene and morpholine, of which morpholine contains about 3...

Embodiment 6

[0072] The morpholine used in embodiment 1 step 1) is changed into the morpholine used in embodiment 1 step 4) and the molar consumption remains unchanged; the toluene used in step 1) and step 3) is all changed into embodiment 1 step 4) reclaim the toluene of gained, volume consumption remains unchanged; All the other are equal to embodiment 1.

[0073] The yield of loxoprofen obtained in step 3) is 77.2%.

Embodiment 7

[0074] Embodiment 7, change the consumption of sodium hydroxide aqueous solution in embodiment 1 step 3), thereby change the mol ratio of sodium hydroxide and N-(1-cyclopentenyl) morpholine; All the other are equal to embodiment 1; Process parameter Shown in table 2 with the contrast of result and embodiment 1.

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Abstract

The invention discloses a synthesis method of loxoprofen sodium, which comprises the following steps of: step 1), preparing N-(1-cyclopentenyl) morpholine; step 2), preparing 2-(4-bromomethyl phenyl)methyl propionate, the method also comprises the following step 3), preparing loxoprofen sodium by an enamine alkylation method: first dissolving 2-(4-bromomethyl phenyl) methyl propionate in a solvent, adding N-(1-cyclopentenyl) morpholine and the solvent in a container, dropwise adding 2-(4-bromomethyl phenyl) methyl propionate solution under reflux conditions; continuing reacting under reflux conditions after the completion of the dropwise addition; adding alkali solution after obtained reaction liquid is cooled, hydrolysising and separating to obtain an organic phase and an aqueous phase respectively, extracting the aqueous phase with an extractant to obtain extract liquid and the aqueous phase after extraction respectively, and post-treating the aqueous phase after extraction to obtain loxoprofen sodium. The preparation of loxoprofen sodium by the above method has the advantages of simple reaction steps, high yield of loxoprofen sodium and low production cost.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a method for synthesizing loxoprofen sodium. Background technique [0002] Loxoprofen sodium, the chemical name is 2-[4-(2-oxocyclopentane-1-ylmethyl)phenyl]sodium propionate, the CAS number is 80382-23-6, and the molecular formula is C 15 h 17 o 3 2H 2 O, with a molecular weight of 304.32 and a structural formula as shown in Formula 1, has obvious analgesic, antipyretic and anti-inflammatory effects, and is a good non-steroidal anti-inflammatory drug. [0003] [0004] Currently, the production of loxoprofen sodium mainly has the following methods: [0005] Document 1 (Synthetic Communications, 1984, 14 (14): 1365-1371) 2-benzyl cyclopentanone and acetyl chloride are catalyzed by aluminum trichloride to generate 2-[(4-acetylphenyl) methyl base] cyclopentanone, which reacts with lithium cyanide and diethyl cyanophosphate (DEPC) to generate compound 1, and compound 1 is hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/02C07C51/41C07C51/09C07C59/86C07D295/033C07C67/08C07C69/65
Inventor 陈新志张哲明钱超
Owner ZHEJIANG UNIV
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