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Method for synthesizing N-cyclopropyl-trans-2-cis-6-nonadienoic acid acidamide

A technology for the synthesis of nonadienyl acid amides, which is applied to the preparation of carboxylic acid amides, chemical instruments and methods, and pharmaceutical formulations. It can solve problems such as complex operations and low reaction yields, and achieve high product yields and excellent reaction conditions mild effect

Inactive Publication Date: 2009-08-12
SHANGHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims at the above-mentioned problems such as complicated operation and low reaction yield, and provides a synthetic method of N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide with mild conditions, easy operation and high reaction yield

Method used

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  • Method for synthesizing N-cyclopropyl-trans-2-cis-6-nonadienoic acid acidamide
  • Method for synthesizing N-cyclopropyl-trans-2-cis-6-nonadienoic acid acidamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: Preparation of trans-2-cis-6-nonadienoic acid

[0029] In a 500mL three-necked flask equipped with a stirrer, a thermometer and a condenser tube, add 22.4g (0.2mol) cis-4-heptenal, 41.6g (0.4mol) malonic acid and 100mL pyridine, and add Inject 2.5mL of hexahydropyridine, raise the temperature to 65°C, react for 4h, TLC detects that the reaction is complete, cool the reaction solution, pour it into a mixture of ice and water containing 500mL of 1N concentrated hydrochloric acid, extract with ether, and wash twice with water. The organic phase was distilled under normal pressure to recover diethyl ether, and the fraction at 102-103° C. / 0.5 mmHg was collected through vacuum distillation to obtain 26.2 g of the product with a yield of 85%.

[0030] The second step: the preparation of trans-2-cis-6-nonadienoyl chloride intermediate product:

[0031] In a 500mL three-necked flask equipped with a stirrer, a thermometer, a dropping funnel and an exhaust gas absorption ...

Embodiment 2

[0035] Step 1: Preparation of trans-2-cis-6-nonadienoic acid

[0036] In a 500mL three-necked flask equipped with a stirrer, a thermometer and a condenser tube, add 22.4g (0.2mol) cis-4-heptenal, 20.8g (0.2mol) malonic acid, 20.4g (0.2mol) basic oxidation Aluminum and 100mL chloroform were heated to reflux for 7 hours. TLC detected that the reaction was complete. Cool the reaction solution, filter off alumina, pour it into a mixture of ice and water containing 500mL of 1N concentrated hydrochloric acid, extract with ether, and wash twice with water. The organic phase was distilled under normal pressure to recover diethyl ether, and the fraction at 102-103° C. / 0.5 mmHg was collected through vacuum distillation to obtain 22.0 g of the product with a yield of 71%.

[0037] The second step: the preparation of trans-2-cis-6-nonadienoyl chloride:

[0038] In a 500mL three-necked flask equipped with a stirrer, a thermometer, a dropping funnel and an exhaust gas absorption device, ad...

Embodiment 3

[0041] Step 1: Preparation of trans-2-cis-6-nonadienoic acid

[0042] In a 500mL three-necked flask equipped with a stirrer, a thermometer and a condenser tube, add 22.4g (0.2mol) cis-4-heptenal, 20.8g (0.2mol) malonic acid, 2.5mL aniline and 100mL chloroform, and heat to reflux After reacting for 7 hours, TLC detected that the reaction was complete, cooled the reaction solution, poured it into a mixture of ice and water containing 500 mL of 1N concentrated hydrochloric acid, extracted with ether, and washed twice with water. The organic phase was distilled under normal pressure to recover diethyl ether, and the fraction at 102-103° C. / 0.5 mmHg was collected through vacuum distillation to obtain 24.6 g of the product with a yield of 80%.

[0043] The second step: the preparation of trans-2-cis-6-nonadienoyl chloride:

[0044] In a 500mL three-necked flask equipped with a stirrer, a thermometer, a dropping funnel and an exhaust gas absorption device, add 15.4 g (0.1 mol) of tr...

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Abstract

The invention discloses a method for synthesizing meaty spice N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide. The method comprises three steps: firstly, cis-4-heptenal and propane diacid undergo condensation reaction to obtain trans-2-cis-6-nonadienoic acid; secondly, the trans-2-cis-6-nonadienoic acid and oxalyl chloride undergo sulfonyl chlorination to obtain trans-2-cis-6-nonadien acyl chloride; and thirdly, the trans-2-cis-6-nonadien acyl chloride and cyclopropylamine undergo amidation to obtain the target product N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide. The method for synthesizing the N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide has the advantages of easily obtained raw materials, mild reaction conditions and high product yield rate, and the total yield rate is about 60 percent. The N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide can be used for enhancing the taste and feeling in food, chewing gums, medicinal products, toothpaste, alcohol drinks.

Description

technical field [0001] The invention relates to a synthesis method of N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide. Background technique [0002] N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide is a new type of food spice, which has a meaty and delicious effect, and can be used in food, chewing gum, medicinal products, toothpaste, alcoholic beverages to enhance taste and Feel. At present, the synthetic method of N-cyclopropyl-trans-2-cis-6-nonadienoic acid amide mainly adopts the mixed anhydride method: in the presence of triethylamine, trans-2-cis-6-nonadiene The acid is reacted with ethyl chloroformate, and the obtained mixed acid anhydride intermediate is further reacted with cyclopropylamine to obtain the target product. This method is complicated to operate and the reaction yield is low (patent document CN1593230, product yield 49%). Contents of the invention [0003] Aiming at the problems of complicated operation and low reaction yield, the present invent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/09C07C231/02A23L1/231A23L2/52A61K8/42A61K47/16C12G3/06A23L27/26
Inventor 李云霞戴晖章平毅陆欢
Owner SHANGHAI INST OF TECH
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