5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid as well as synthetic method and application thereof

A technology of dimethyl bromomethylisophthalate and isophthalic acid, applied in the field of 5-methyl)isophthalic acid and its synthesis, can solve the problem of not retrieving the isophthalic acid compound literature report, not yet Find the problems such as 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid, and achieve the effect of few reaction steps and high yield

Inactive Publication Date: 2014-10-08
天津致嫣达远科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 5-((2-carboxypiperidin-1-yl) methyl) isophthalic acid invented by the present invention is a novel ternary organic carboxylic acid. So far, no 5-((2-carboxy The compound of piperidin-1-yl)methyl)isophthalic acid, and the literature report of 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid compound has not been retrieved

Method used

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  • 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid as well as synthetic method and application thereof
  • 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid as well as synthetic method and application thereof
  • 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid as well as synthetic method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Step 1: Synthesis of dimethyl 5-((2-methoxycarbonylpiperidin-1-yl)methyl)isophthalate:

[0033] In a 25 mL single-necked flask, weigh methyl 2-piperidinecarboxylate (0.286 g, 2 mmol), dimethyl 5-bromomethylisophthalate (0.572 g, 2 mmol), potassium carbonate (0.414 g, 3 mmol), dissolved in 10 mL of acetonitrile, stirred at room temperature for 16 hours, TLC monitored the reaction was complete, and stopped stirring. Concentrate the reaction solution with a rotary evaporator, extract with ethyl acetate, wash the reaction solution with water to remove excess potassium carbonate, and wash with anhydrous NaSO 4 The organic layer was dried, filtered, and suspended to dryness to obtain dimethyl 5-((2-methoxycarbonylpiperidin-1-yl)methyl)isophthalate as a pale yellow liquid with a yield of 91%.

Embodiment 2

[0035] Step 2: Synthesis of 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid:

[0036] In a 25 mL single-necked flask equipped with a reflux condenser, the dimethyl 5-((2-methoxycarbonylpiperidin-1-yl)methyl)isophthalate (0.503 g, 1.5 mmol), be dissolved in 2mL water, add potassium hydroxide (0.337 g, 6 mmol), reflux reaction after 6 hours, TLC monitoring reaction is complete, reaction solution is cooled to room temperature, washes with ethyl acetate to remove a small amount of unreacted raw material, Keep the aqueous phase. Then slowly add 1M hydrochloric acid dropwise to adjust the pH of the reaction solution to 3-4. At this time, a large amount of solids precipitated. The precipitated solids were filtered and dried in vacuo to obtain 5-((2-carboxypiperidin-1-yl)methanol Base) isophthalic acid, melting point: 212-214 ° C, yield is 75%. The NMR spectrum of 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid compound-H figure 1 .

Embodiment 3

[0038] Step 1: Synthesis of dimethyl 5-((2-methoxycarbonylpiperidin-1-yl)methyl)isophthalate:

[0039] In a 25 mL single-necked flask, weigh methyl 2-piperidinecarboxylate (0.286 g, 2 mmol), dimethyl 5-bromomethylisophthalate (0.315 g, 2.2 mmol), potassium carbonate (0.276 g, 2mmol), dissolved in 10mL of acetonitrile, stirred at room temperature for 18 hours, TLC monitoring of complete reaction, stop stirring. Concentrate the reaction solution with a rotary evaporator, extract with ethyl acetate, wash the reaction solution with water to remove excess potassium carbonate, dry the organic layer with anhydrous NaSO, filter, and hang to dryness to obtain 5-((2-methoxycarbonylpiperidine- 1-yl) methyl) dimethyl isophthalate, as light yellow oily liquid, the yield is 89%.

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Abstract

The invention discloses 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid as well as a synthetic method and an application thereof. The synthetic method comprises the following steps of reacting dimethyl 5-(bromomethyl)isophthalate with methyl 2-piperidinecarboxylate to obtain dimethyl 5-((2-methoxycarbonylpiperidin-1-yl) methyl) isophthalate; then carrying out hydrolysis reaction on dimethyl 5-((2-methoxycarbonylpiperidin-1-yl) methyl) isophthalate under a basic condition and then carrying out acidic adjustment on the reaction solution for precipitating a product, filtering the precipitated solid and drying to obtain the target product. The compound can be used as a hydrophilic chain extender to prepare a waterborne polyurethane emulsion.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing 5-((2-carboxypiperidin-1-yl)methyl)isophthalic acid, more specifically a 5-((2-carboxypiperidin Pyridin-1-yl)methyl)isophthalic acid and its synthesis method and application. Background technique [0002] Carboxylic acid compounds are an important class of organic acid compounds. In recent years, with the deepening of people's understanding of these compounds, their research and application have become more and more extensive and in-depth. In coordination chemistry, carboxylic acid organic ligand compounds are more and more favored by coordination chemistry researchers because of their various ligands, complex coordination modes, and flexible coordination methods. Carboxylic acid organic ligands rely on their subversive nature to compensate the charge of the entire system and reduce the counter ion effect of the system. Secondly, there are ofte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/60C08G18/66C08G18/38
CPCC07D211/60C08G18/10C08G18/3844
Inventor 刘巨艳赵聪颖杨莉
Owner 天津致嫣达远科技发展有限公司
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