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Preparation method of 6-cyclohexyl-3,4-cyclohexyl-5-nitrocaprolactam-4-ene

A nitrogen caprolactam and cyclohexyl technology is applied in the field of synthesis of pharmaceutical intermediates, which can solve the problems of flushing materials, easy occurrence of safety accidents and the like, and achieves the effects of high yield, low cost and moderate reaction conditions.

Inactive Publication Date: 2018-11-30
HEZE CITY FANGMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Later, an improved process appeared at home and abroad, and ammonium carbonate or ammonium bicarbonate was added together with urea to prevent urea from condensing to form biuret, etc. A security incident occurred

Method used

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  • Preparation method of 6-cyclohexyl-3,4-cyclohexyl-5-nitrocaprolactam-4-ene

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] Example 1. Under normal pressure, add 200g of cyclohexanone and 40ml of toluene into a 1000ml flask equipped with a water separator and a condenser, then start stirring, raise the temperature to 135-145°C and reflux for dehydration, and separate the water from the water separator , and then through a triangular funnel with a branch pipe inner diameter of 4mm, continuously add 30g of urea within 1 hour, after adding, maintain the reaction for 1.5 hours, remove 18ml of water, stop heating, add 0.1g of spirocycle crystals to induce crystallization, and then Slowly lower to 20°C, then filter with suction, wash the filter cake with 100g cyclohexanone, the wet weight of the filter cake is 77.5g, the dry weight is 63.1g, the purity is 97.5%, the calculated molar yield is 57.4%, the filter cake can be directly put into the water without drying The first step is the hydrolysis process, and the mother liquor and lotion are put into the next batch of synthesis reaction.

example 2

[0021] Example 2. Under normal pressure, add 260g of the previous batch of mother liquor and lotion into a 1000ml flask equipped with a water separator and a condenser, then start stirring, raise the temperature to 135-145°C for reflux dehydration, and separate out the water separator Water, then through a triangular funnel with a branch pipe inner diameter of 4mm, continuously add 30g of urea within 1 hour, after the addition, maintain the reaction for 1.5 hours, remove 18.5ml of water, stop heating, add 0.1g of spirocycle crystals to induce crystallization , then slowly lowered to room temperature, then suction filtered, washed the filter cake with 100g cyclohexanone, the wet weight of the filter cake was 111.8g, the dry weight was 95.5g, the purity was 97.3%, and the calculated molar yield was 86.8%. The filter cake can be directly put into In the next step of hydrolysis process, the mother liquor and lotion are put into the next batch of synthesis reaction.

example 3

[0022] Example 3. Under normal pressure, add 270g of the previous batch of mother liquor and lotion to a 1000ml flask equipped with a water separator and a condenser, then start stirring, raise the temperature to 135-145°C for reflux dehydration, and separate the water separator Water, then through a triangular funnel with a branch pipe inner diameter of 4mm, continuously add 30g of urea within 1 hour, after the addition, maintain the reaction for 1.5 hours, remove 17ml of water, stop heating, add 0.1g of spirocycle crystals to induce crystallization, Then slowly drop to room temperature, then suction filter, wash the filter cake with 100g cyclohexanone, the wet weight of the filter cake is 112.9g, the dry weight is 88.9g, the purity is 97.2%, and the calculated molar yield is 80.8%. The first step is the hydrolysis process, and the mother liquor and lotion are put into the next batch of synthesis reaction.

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Abstract

The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and discloses a preparation method of 6-cyclohexano-3,4-cyclohexyl-5-N-hexanolactam-4-ene. The preparation method comprises the following processes: firstly putting a previous batch of mother liquid containing quantitative cyclohexanone, a target product, an intermediate component and an inert solvent and a washing liquid into a reactor, starting stirring, heating to 135-145 DEG C, carrying out reflux dehydration, separating water in a dehydrater, further adding a certain amount of urea in a certain time by virtue of a special sealed device, after the addition of urea is completed, further dehydrating until a theoretical amount, stopping heating, carrying out induced crystallization, slowly cooling to room temperature, carrying out solid-liquid separation, washing a filter cake with a consumption amount of cyclohexanone, directly putting the filter cake into a next-step hydrolysis process without drying and feeding the mother liquid and washing liquid into the next batch of synthesis reaction. The process has the advantages of no need of addition of a catalyst, mild reaction conditions, no wastewater, safety and environment friendliness, energy conservation, consumption reduction, high yield, good quality and low cost and can be used for industrial production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 6-cyclohexyl-3,4-cyclohexyl-5-nitrocaprolactam-4-ene. Background technique [0002] 6-cyclohexyl-3,4-cyclohexyl-5-nitrocaprolactam-4-ene is a spiro ring synthesized by 1 molecule of urea and 2 molecules of cyclohexanone. The pure product is a white flaky crystal. The melting point is 210°C. It is an intermediate in the preparation of Gliclazide, a drug for treating type Ⅱ diabetes, and it can also be used in the production of pesticides and herbicides. [0003] The traditional production method is to add a certain amount of cyclohexanone to toluene, then add p-toluenesulfonic acid of 5% of the amount of urea as a catalyst, add 1.08 times the theoretical amount of urea at one time under stirring, and then heat up the dehydration reaction, which takes about 10 For about an hour, under strong acid and high temperature condit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/70
CPCC07D239/70
Inventor 王兴路韩涛范兴山方金印朱文祥
Owner HEZE CITY FANGMING PHARMA
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