CN109467521B - Process for synthesizing 2-cyclamate - Google Patents
Process for synthesizing 2-cyclamate Download PDFInfo
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
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Abstract
The invention discloses a process for synthesizing 2-cyclo-hexylaminoethanesulfonic acid, which comprises the following steps: heating cyclohexylamine, dripping heated aqueous solution of 2-chloroethyl sodium sulfonate, stirring, heating to reflux, adding 1-3 wt% of active carbon, filtering while hot after reflux, concentrating, adding ethanol, and adjusting pH to 5.0-6.0 with glacial acetic acid; adding ethanol with the volume 1-1.5 times that of the filtrate, cooling and filtering; adding the filter residue into hot ethanol, refluxing, adding water, filtering while hot, cooling to 5-10 deg.C, filtering, washing the filter residue with ethanol, and drying to obtain 2-cyclamate. The synthesis process provided by the invention has relatively high yield and good purity.
Description
Technical Field
The invention relates to a synthesis method of a drug intermediate, in particular to a process for synthesizing 2-cyclo-hexylaminoethanesulfonic acid.
Background
In biochemical and molecular biological experiments, a series of buffers have wide application range, and a zwitterionic buffer, namely Good's buffer, is a series of N-substituted sulfamic acid, has Good pH stability and high polarity, and is inert to various chemical reagents and enzymes.
CHES products having a pKa value of 9.5 at 25 ℃ and a pH buffer in the range of 8.6-10.0 are zwitterionic buffers used in the biochemistry of biochemistry and, although not introduced by Good et al, are referred to as Good's buffers. The application range is as follows:
1) as a buffer for the enzymatic reaction;
2) samples and running buffers for various capillary electrophoresis;
3) exhibits high affinity for the iodoacetate binding site of hepatic alcohol dehydrogenase, protecting the enzyme from inactivation by iodoacetate;
4) phosphodiesterase has the greatest activity in CHES compared to other buffers;
5) CHES can inhibit the viability of Micrococcus luteus at pH 9.5.
Optimizing the reaction conditions of the CHES original process, comparing different conditions of the purity of the crude product obtained by the reaction, and optimizing and screening the optimal reaction conditions. Finally, the process is stabilized, the scale-up production is facilitated, the reaction yield is improved, and the production cost is reduced.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a process for synthesizing 2-cyclamate, the yield of which is greatly improved.
The purpose of the invention is realized by adopting the following technical scheme:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating cyclohexylamine to 45-55 ℃, then dropwise adding a thermally dissolved 50-60 wt% aqueous solution of 2-chloroethyl sodium sulfonate, stirring and heating to reflux;
2) cooling the reaction liquid obtained in the step 1), adding 1-3 wt% of activated carbon, and performing complete reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 10-20 vt% of the original volume, adding ethanol with the volume 3-8 times that of the concentrated solution, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding ethanol 1-1.5 times the volume of the filtrate, cooling to 5-10 deg.C, and filtering;
4) adding the filter residue obtained in the step 3) into hot ethanol with the weight of 1.4-2.0 times of that of the filter residue, heating to reflux, adding water with the weight of 15-25% of the filter residue, filtering while hot, cooling to 5-10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain the 2-cyclicaminoethanesulfonic acid.
Further, in the step 1), the molar ratio of the cyclohexylamine to the sodium 2-chloroethyl sulfonate is 1 (0.95-0.98).
Further, in step 2), 2 wt% of activated carbon was added.
Further, the method comprises the following steps:
1) heating 1mol of cyclohexylamine to 45-55 ℃, then dropwise adding a solution formed by dissolving 0.96mol of thermally dissolved 2-chloroethyl sodium sulfonate in 160-170mL of water, stirring and heating to reflux;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 40-50mL, adding 160-200mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 35-40mL of ethanol, cooling to 5-10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 300mL of hot ethanol of 250-300mL, heating to reflux, adding 35-40mL of water, filtering while hot, cooling to 5-10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain the 2-cyclicaminoethanesulfonic acid.
Further, the method also comprises the step 5): concentrating the filtrate obtained in step 4) to 40-50% volume, filtering, adding 1.4-2.0 times weight of hot ethanol into the filter residue, heating to reflux, adding 15-25% weight of water into the filter residue, filtering while hot, cooling to 5-10 deg.C, filtering, washing the filter residue with ethanol, and drying.
Compared with the prior art, the invention has the beneficial effects that:
1) the process for synthesizing 2-cyclohexylaminoethanesulfonic acid provided by the invention can effectively improve the reaction degree of the 2-chloroethanesulfonic acid sodium and the cyclohexylamine by dissolving the 2-chloroethanesulfonic acid sodium in water under a hot condition and then dripping the 2-chloroethanesulfonic acid sodium into the hot cyclohexylamine, thereby improving the reaction yield;
2) according to the invention, the unreacted sodium 2-chloroethyl sulfonate and the cyclohexylamine are continuously reacted by adding the activated carbon and then carrying out heat preservation reflux reaction, so that the yield and the product purity are improved;
3) according to the invention, the crude product is purified again by taking ethanol and water as a mixed solvent, so that the purity of the 2-cyclo-hexylaminoethanesulfonic acid product is effectively improved.
Detailed Description
The present invention is further described below with reference to specific embodiments, and it should be noted that, without conflict, any combination between the embodiments or technical features described below may form a new embodiment.
The invention provides a process for synthesizing 2-cyclamate, which comprises the following steps:
1) heating cyclohexylamine to 45-55 ℃, then dropwise adding a thermally dissolved 50-60 wt% aqueous solution of 2-chloroethyl sodium sulfonate, stirring and heating to reflux;
2) cooling the reaction liquid obtained in the step 1), adding 1-3 wt% of activated carbon, and performing complete reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 10-20 vt% of the original volume, adding ethanol with the volume 3-8 times that of the concentrated solution, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding ethanol 1-1.5 times the volume of the filtrate, cooling to 5-10 deg.C, and filtering;
4) adding the filter residue obtained in the step 3) into hot ethanol with the weight of 1.4-2.0 times of that of the filter residue, heating to reflux, adding water with the weight of 15-25% of the filter residue, filtering while hot, cooling to 5-10 ℃, filtering, washing the filtrate with ethanol, and drying to obtain the 2-cyclicaminoethanesulfonic acid.
Example 1:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 99g (1mol) of cyclohexylamine to 50 ℃, dripping 180g (0.96mol) of 2-chloroethyl sodium sulfonate dissolved at 85 ℃ into 166mL of water to form a solution, and stirring and heating until reflux reaction is carried out for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 46.4g (0.188mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 10.7g (0.043mol) of 2-cyclamate with the HPLC purity of 98%.
Example 2:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 99g (1mol) of cyclohexylamine to 50 ℃, then dropwise adding a solution formed by dissolving 181g (0.98mol) of thermally dissolved 2-chloroethyl sodium sulfonate in 170mL of water, stirring and heating until reflux reaction is carried out for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 48mL, adding 200mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 35mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 45.0g (0.182mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 170mL, filtering, adding filter residue into 120mL of hot ethanol, heating to reflux, adding 16mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 10.9g (0.044mol) of 2-cyclamate with the HPLC purity of 98%.
Example 3:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 99g (1mol) of cyclohexylamine to 50 ℃, then dropwise adding a solution formed by dissolving 175g (0.95mol) of thermally dissolved 2-chloroethyl sodium sulfonate in 170mL of water, stirring and heating until reflux reaction is carried out for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5g of activated carbon, and performing reflux reaction completely;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 170mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 35mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 300mL of hot ethanol, heating to reflux, adding 40mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 48.2g (0.195mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 150mL, filtering, adding filter residue into 120mL of hot ethanol, heating to reflux, adding 16mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 10.4g (0.042mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 1:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate and 170mL of water to 85 ℃, adding 99g (1mol) of cyclohexylamine in batches, stirring, heating to reflux and reacting for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 39.7g (0.161mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.36g (0.038mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 2:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate and 170mL of water to 85 ℃, adding 99g (1mol) of cyclohexylamine in batches, stirring, heating to reflux and reacting for 20 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 39.9g (0.162mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.77g (0.040mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 3:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate, 9g of sodium carbonate and 170mL of water to 85 ℃, adding 99g (1mol) of cyclohexylamine in batches, stirring, heating to reflux and reacting for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 40.8g (0.165mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.86g (0.040mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 4:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate, 9g of potassium carbonate and 170mL of water to 85 ℃, adding 99g (1mol) of cyclohexylamine in batches, stirring and heating to reflux reaction for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 40.2g (0.163mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.96g (0.040mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 5:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate, 9g of potassium carbonate and 170mL of water to 85 ℃, adding a mixed solution of 99g (1mol) of cyclohexylamine and 10g of ethanol in batches, stirring and heating until reflux reaction is carried out for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 40.9g (0.166mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.91g (0.040mol) of 2-cyclamate with the HPLC purity of 98%.
Comparative example 6:
a process for synthesizing 2-cyclamate comprises the following steps:
1) heating 175g (0.95mol) of 2-chloroethyl sodium sulfonate, 9g of potassium iodide and 170mL of water to 85 ℃, adding a mixed solution of 99g (1mol) of cyclohexylamine and 10g of ethanol in batches, stirring and heating until reflux reaction is carried out for 6 hours;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 45mL, adding 180mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 38mL of ethanol, cooling to 10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 280mL of hot ethanol, heating to reflux, adding 38mL of water, filtering while the filter residue is hot, cooling to 10 ℃, filtering, washing the filtrate with cold ethanol, and drying to obtain 40.1g (0.162mol) of 2-cyclamate, wherein the HPLC purity is 98%;
step 5): concentrating the filtrate obtained in the step 4) to 160mL, filtering, adding filter residue into 110mL of hot ethanol, heating to reflux, adding 15mL of water, filtering while hot, cooling to 10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain 9.82g (0.040mol) of 2-cyclamate with the HPLC purity of 98%.
The above embodiments are only preferred embodiments of the present invention, and the protection scope of the present invention is not limited thereby, and any insubstantial changes and substitutions made by those skilled in the art based on the present invention are within the protection scope of the present invention.
Claims (4)
1. A process for synthesizing 2-cyclamate comprises the following steps:
1) heating cyclohexylamine to 45-55 ℃, then dropwise adding a thermally dissolved 50-60 wt% aqueous solution of 2-chloroethyl sodium sulfonate, stirring and heating to reflux; the molar ratio of the cyclohexylamine to the 2-chloroethyl sodium sulfonate is 1 (0.95-0.98);
2) cooling the reaction liquid obtained in the step 1), adding 1-3 wt% of activated carbon, and performing complete reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 10-20 vt% of the original volume, adding ethanol with the volume 3-8 times that of the concentrated solution, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding ethanol 1-1.5 times the volume of the filtrate, cooling to 5-10 deg.C, and filtering;
4) adding the filter residue obtained in the step 3) into hot ethanol with the weight of 1.4-2.0 times of that of the filter residue, heating to reflux, adding water with the weight of 15-25% of the filter residue, filtering while hot, cooling to 5-10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain the 2-cyclicaminoethanesulfonic acid.
2. The process of claim 1, wherein in step 2), 2 wt% of activated carbon is added.
3. The process of claim 1, comprising the steps of:
1) heating 1mol of cyclohexylamine to 45-55 ℃, then dropwise adding a solution formed by dissolving 0.96mol of thermally dissolved 2-chloroethyl sodium sulfonate in 160-170mL of water, stirring and heating to reflux;
2) cooling the reaction liquid obtained in the step 1), adding 5.5g of activated carbon, and completely performing reflux reaction;
3) filtering the reaction solution obtained in the step 2) while the reaction solution is hot, concentrating the filtrate to 40-50mL, adding 160-200mL of ethanol, and adjusting the pH value to 5.0-6.0 by using glacial acetic acid; adding 35-40mL of ethanol, cooling to 5-10 ℃, and filtering;
4) adding the filter residue obtained in the step 3) into 300mL of hot ethanol of 250-300mL, heating to reflux, adding 35-40mL of water, filtering while hot, cooling to 5-10 ℃, filtering, washing the filter residue with ethanol, and drying to obtain the 2-cyclicaminoethanesulfonic acid.
4. The process according to any one of claims 1 to 3, further comprising step 5): concentrating the filtrate obtained in step 4) to 40-50% volume, filtering, adding 1.4-2.0 times weight of hot ethanol into the filter residue, heating to reflux, adding 15-25% weight of water into the filter residue, filtering while hot, cooling to 5-10 deg.C, filtering, washing the filter residue with ethanol, and drying.
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