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Preparation method for intermediate II during meptazinol hydrochloride synthesis process

A technology of the synthetic process of mebutamol hydrochloride, which is applied in the direction of organic chemistry, etc., to achieve the effects of high yield, shortened time, and simple operation

Inactive Publication Date: 2012-12-26
YANGTZE RIVER PHARM GRP SICHUAN HAIRONG PHARM CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0007] Using the prior art, 1.3-cyclohexanedione is catalyzed by p-toluenesulfonic acid, and 3-isopropoxyaldehyde-2-cyclohexenone is generated with isopropanol, and its follow-up process needs to be filled with molecular sieves Reaction in Soxhlet extraction device, and the yield of intermediate 3-isopropoxycyclohexenone is only 65%

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  • Preparation method for intermediate II during meptazinol hydrochloride synthesis process
  • Preparation method for intermediate II during meptazinol hydrochloride synthesis process
  • Preparation method for intermediate II during meptazinol hydrochloride synthesis process

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Embodiment Construction

[0017] Below, in conjunction with embodiment the content of the present invention is described in detail.

[0018] (1) Preparation of 3-methoxy-2-cyclohexenone (intermediate I)

[0019]

[0020] 1. Feeding ratio:

[0021] 1,3-cyclohexanedione FW=112.05 1800g 16mol

[0022] Methanol FW=32.03 4500g 140mol

[0023] Chloroform d=1.47 24000-28000ml

[0024] 2. Operation steps:

[0025] Add 1,3-cyclohexanedione, chloroform, methanol and 20g of p-toluenesulfonic acid into the reaction flask in sequence, heat up to boiling with stirring, and slowly distill out about 20000ml of distillate, which takes 5 to 7 hours. Remove from heat and cool to room temperature. Samples were taken by TLC to confirm that the reaction was normal and post-processed. Wash the residue with 10000ml of 10% sodium hydroxide for 3 times, combine the lye layers, and extract with 3000ml of distilled liquid. The organic layers were combined, washed with saturated brine 2000ml*2 until neutral, and dried ov...

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Abstract

The present invention discloses a preparation method for a meptazinol hydrochloride intermediate II hexahydro-1-methyl-3-(3-oxo-1-cyclohexen-1-yl)-2H-azepin-2-one. According to the present invention, methanol is adopted to replace isopropanol to complete synthesis of an intermediate I 3-methoxy-2-cyclohexenone in the prior art, hydrochloric acid is slowly added to the material in a dropwise manner during the intermediate II synthesis process, and chloroform is adopted to extract the product (wherein the chloroform is more easily recovered than dichloromethane). The preparation process of the present invention has characteristics of mild production condition requirements, simple operation, high yield, and easily-recovered solvent.

Description

technical field [0001] The invention relates to the field of chemical pharmacy. Especially the synthesis process of mebutamol hydrochloride. Background technique [0002] The chemical name of meptafol hydrochloride is: 3-(1'-methyl-3'-ethyl-1H-hexahydroazepine-3'-yl)phenol hydrochloride [0003] [0004] Mebutaol is a potent agonist-antagonist analgesic drug (an agonist of the opioid μ receptor and an antagonist of the μ receptor. It is a potent analgesic drug), developed by Wyeth (UK), and was developed in 1986 in Listed in the UK for the first time, it was recorded in the British Pharmacopoeia in 1998. [0005] Meprotamol takes 1,3-cyclohexanedione (17) as raw material and mainly has the following synthetic routes: [0006] 1,3-cyclohexanedione (17) is a raw material, reacts with isopropanol under the catalysis of p-toluenesulfonic acid to obtain 3-isopropoxycyclohexenone (19), and then reacts with N- Condensation of methylcaprolactam to 1-methyl-3-(3-oxocyclohexen-...

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Application Information

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IPC IPC(8): C07D223/10
Inventor 廖建袁道义马茂华罗凯华
Owner YANGTZE RIVER PHARM GRP SICHUAN HAIRONG PHARM CO LTD
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