CN104496825A - Preparation method of 2-fluoroethylamine hydrochloride - Google Patents
Preparation method of 2-fluoroethylamine hydrochloride Download PDFInfo
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Abstract
The invention relates to a preparation method of 2-fluoroethylamine hydrochloride, which is characterized in that 2-fluoroethanol and toluene sulfochloride are reacted, hydrogen chloride gas in a reaction solution can be eliminated by conventional nitrogen, processes such as extraction can be avoided, and extraction can be prevented. According to the invention, integral reaction time is optimized, equipment utilization rate is increased, more important, through ethanol and water extraction for impurities removal, content of the obtained product is high (99%), the yield is increased, the raw material price is cheap and easily available, and no pollution is generated. Therefore, the cost is reduced, and the output of the final product is greatly increased.
Description
Technical field
The present invention relates to a kind of compounds process for production thereof, particularly relate to a kind of preparation method of 2-fluorine ethylamine hydrochloride.
Background technology
Existing 2-fluorine ethylamine hydrochloride, needs in its preparation process to adopt sodium carbonate to wash, washing, and also need to carry out subtracting steaming and just can obtain intermediate 1. and need Vanadium Pentoxide in FLAKES dry in subsequent filter washing, crystallization obtains product, yield about 50%.In follow-up preparation, also must adopt then with salicylic aldehyde, ether, benzene equal solvent purified product, cause yield to reduce further, only have 35%.For this reason, the time of manufacture is long, complex process, and input cost is large, is unfavorable for promoting.
Summary of the invention
Object of the present invention is exactly to solve the above-mentioned problems in the prior art, provides a kind of preparation method of 2-fluorine ethylamine hydrochloride.
Object of the present invention is achieved through the following technical solutions:
The preparation method of 2-fluorine ethylamine hydrochloride, is characterized in that comprising the following steps:
1. step, puts into quantitative 2-fluoroethanol and toluene sulfonyl chloride in the first reaction vessel, carries out reacting by heating, stop after completion of the reaction after drying protection;
2. step, carries out recovery 2-fluoroethanol by distillation, introduces rare gas element, and blowout HCl gas, obtains mesosome 1 through underpressure distillation;
3. step, carries out reacting by heating after adding intermediate 1, potassium phthalimide, DMF in the second reaction vessel, follows the tracks of reaction process and reacts completely to intermediate 1, termination reaction immediately by a plate;
4., carry out being cooled to 80 DEG C to 90 DEG C, reaction solution step 3. obtained is poured into water and stirs step, carry out freeze overnight afterwards, after to be filtered, obtain fluffy solid, dry after washing, by ethyl alcohol recrystallization, obtain the intermediate 2 of white needle-like crystals;
Step 5., intermediate 2, ethanol is added in the 3rd reaction vessel, by heating after dry-run protection, intermediate 2 is made to be dissolved completely in ethanol, after waiting for reaction solution cooling, add hydrazine hydrate, carry out heating reflux reaction, stop after the completely dissolve of question response raw material, after carrying out cooling twice, carry out PH adjustment, then carry out stopped reaction after heating reflux reaction;
6. step, cools the reaction solution that 5. step obtains, and adds water and stirs, filter, concentrated filtrate; Again add water and carry out secondary stirring, again filter, after concentrated filtrate is extremely dry, obtain solid;
7., dissolution of solid step 6. obtained in ethanol, carries out ice bath stirring to step, obtains white powder solid or white flaky crystals, after super-dry, obtain final finished after cold filtration.
The preparation method of above-mentioned 2-fluorine ethylamine hydrochloride; wherein: described step 1. in; first reaction vessel is the there-necked flask of 500ml; the quantitative factor of described 2-fluoroethanol is 130 to 160g; the quantitative factor of described toluene sulfonyl chloride is 160 to 190g; described dry-run protection is realized by drying tube protection, and described heat-processed is employing 90 to 120 DEG C of heating reflux reactions 5 to 11 hours.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: described step 1. in, after reacting by heating, shown by TLC plate, checking Tosyl chloride react completely.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: step 2. described revolving is steamed temperature and is 40 to 70 DEG C, and reduces pressure during revolving steaming, and described underpressure distillation adopts 10 to 20mmHg, carries out at 135 to 142 DEG C.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: step 3. described in the second reaction vessel be the there-necked flask of 2L, the content of intermediate 1 is 130 to 160g, the content of potassium phthalimide is 120 to 130g, the content of DMF is 500 to 1600ml, is heated to 80 to 120 DEG C of reactions 30 to 45 minutes.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: the 4. described reaction solution of step is poured in 2000 to 3000mlL water, stir 5min, the temperature of freeze overnight is 8 to 10 DEG C, and bake out temperature is 60 to 80 DEG C, by the ethyl alcohol recrystallization of 500 to 800ml.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: described step 5. in, 3rd reaction vessel is the there-necked flask of 250ml, the amount adding intermediate 2 is 30 to 60g, the ethanol adopted is 300 to 500ml, dry-run protection is carried out by drying tube, be heated to 70 to 80 DEG C, add hydrazine hydrate 20 to 30g, 17.8g, be heated to 80 to 81 DEG C of back flow reaction about 1 to 2 hour, by a plate detection reaction raw material completely dissolve, then stopped reaction, after question response liquid is cooled to 60 DEG C, add concentrated hydrochloric acid 10 to 30ml, regulate PH to 2, back flow reaction stopped reaction after 1 to 2 hour again.
Further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: described step 6. in, the reaction solution cooling 5. obtained step, after adding 100 to 200ml water, stirs, filtered, concentrated filtrate.Again add 500 to 800ml water, stir, filter, concentrated, obtain solid.
Again further, the preparation method of above-mentioned 2-fluorine ethylamine hydrochloride, wherein: described step 7. in, adopt 100-200ml ethanol, stirs 2 hours, filter, drying, obtains final finished after oven dry.
The advantage of technical solution of the present invention is mainly reflected in: optimize technique and reclaim, improve overall yield.Meanwhile, can adopt the hydrogen chloride gas in conventional nitrogen eliminating reaction solution, what avoid extraction waits operation, removes the employing of extraction from.Further, optimize the overall reaction times, improve plant factor.What is more important, by ethanol and water extraction impurity removing technology, the product content not only obtained high (99%), and yield improves, and both not only cost of material is cheap, be easy to get, pollution-free.Thus, while minimizing cost, the output of final thing is significantly increased.
Embodiment
The preparation method of 2-fluorine ethylamine hydrochloride, it comprises the following steps:
First, in the first reaction vessel, put into quantitative 2-fluoroethanol and toluene sulfonyl chloride, carry out reacting by heating after drying protection, stop after completion of the reaction.Specifically, in order to have preferably reaction effect, this first reaction vessel is the there-necked flask of 500ml, and the quantitative factor of the 2-fluoroethanol adopted is 130 to 160g.Meanwhile, the quantitative factor of toluene sulfonyl chloride is 160-190g, and dry-run protection is realized by drying tube protection.Further, consider that reaction output efficiency improves, heat-processed is employing 90 to 120 DEG C, heating reflux reaction 5 to 11 hours.Certainly, consider the effective checking reacted completely, after reacting by heating, reacted completely by TLC display checking Tosyl chloride.Compare by repeatedly reacting, its preferred scheme is, the consumption of 2-fluoroethanol is 150g, 2.343mol, and the quantitative factor of toluene sulfonyl chloride is 180g, 0.947mol.Preferred Heating temperature is 113 DEG C and carried out heating reflux reaction by 10 hours.
Afterwards, carry out the recovery of 2-fluoroethanol, import the rare gas element of such as nitrogen etc. by distillation, blowout HCl gas, obtains mesosome 1 through distillation.Specifically, in order to effectively blow out HCl gas, the distillation temperature of employing is 40 to 70 DEG C, and reduces pressure during distillation, and underpressure distillation adopts 10 to 20mmHg, carries out at 135 to 142 DEG C.Further, preferred distillation temperature is good with 60 DEG C, and thus, in conjunction with previous preferred version, overall obtained fine work intermediate 1 about 185g, yield can reach 89.5%.
Then, add intermediate 1, potassium phthalimide, DMF in the second reaction vessel after, carry out reacting by heating, follow the tracks of reaction process by a plate and react completely to intermediate 1, termination reaction immediately.Specifically, use the there-necked flask of 2L as the second reaction vessel.Meanwhile, select the potassium phthalimide of the intermediate 1,120 to 130g of 130 to 160g, and the content of DMF is 500 to 1600ml, is heated to 80 to 120 DEG C of reactions 30 to 45 minutes.
Certainly, in order to provide comparatively preferred scheme, the content of intermediate 1 can adopt 2g, 0.697mol, and the content of potassium phthalimide is the content of 128.98g, 0.697mol, DMF is 1500ml, after being heated to 110 DEG C, reacts 35 minutes.
Subsequently, be cooled to 80 DEG C to 90 DEG C, the reaction solution of acquisition is poured into water, stir.Hold over night afterwards, after filtration, obtains fluffy solid.Dry after washing, by ethyl alcohol recrystallization, the intermediate 2 of white needle-like crystals can be obtained.In this layoutprocedure, reaction solution is poured in 2000 to 3000ml water, stir 5min.Adopt, bake out temperature is 70 to 80 DEG C, by the ethyl alcohol recrystallization of 500 to 800ml.Meanwhile, comparatively preferred embodiment can obtain the intermediate 2 of about 113g, yield is 85%.
Then, adopt the there-necked flask of 250ml to add the intermediate 2 of 30 to 60g, the ethanol of 300 to 500ml in this embodiment as the 3rd reaction vessel, by dry-run protection post-heating to 70 to 80 DEG C, make intermediate 2 be dissolved completely in ethanol.After waiting for reaction solution cooling, add the hydrazine hydrate of 20 to 30g, at the temperature of 80 to 81 DEG C, carry out heating reflux reaction 1 to 2 hour.Afterwards, stop after the completely dissolve of question response raw material, after carrying out cooling twice to 60 DEG C, add concentrated hydrochloric acid 10 to 30ml, regulate PH to approximate 2.Finally, then carry out heating reflux reaction stopped reaction after 1 to 2 hour.
During this period, the preferred amounts of intermediate 2 is 50g, 0.259mol, and the ethanol preferred amounts of employing is 350ml, and the preferred amounts of hydrazine hydrate is 25g.Meanwhile, by a plate detection reaction raw material completely dissolve.
Immediately, cool, add 100 to 200ml water, agitation and filtration, concentrated filtrate, again add 500 to 800ml water the reaction solution previously obtained, stir, filter, condensed water filtrate again, can obtain solid.
Finally, by this dissolution of solid in 100-200ml ethanol, carry out stirring 2 hours, filter, rear acquisition white powder solid or white flaky crystals, by drying, design temperature 70 to 80 DEG C obtains final finished after drying.The product of preferred acquisition is about 23g, and yield can reach 89.7% substantially.
" embodiment one "
The preparation method of 2-fluorine ethylamine hydrochloride, it adopts following steps:
First, in the first reaction vessel, put into quantitative 2-fluoroethanol and toluene sulfonyl chloride, carry out reacting by heating after drying protection, stop after completion of the reaction.Specifically, in order to have preferably reaction effect, this first reaction vessel is the there-necked flask of 500ml, and the quantitative factor of the 2-fluoroethanol adopted is 130g.Meanwhile, the quantitative factor of toluene sulfonyl chloride is 160g, and drying tube carries out dry-run protection.The temperature of heating is 90 DEG C, heating reflux reaction 5 hours.After reacting by heating, reacted completely by TLC display checking Tosyl chloride.
Afterwards, carry out the recovery of 2-fluoroethanol, blast the rare gas element of such as nitrogen etc. by distillation, blowout HCl gas, obtains mesosome 1 through distillation.Specifically, employing revolve steam temperature be 40 DEG C, underpressure distillation adopts 1 mmHg, carries out at 135 DEG C.
Then, add intermediate 1, potassium phthalimide, DMF in the second reaction vessel after, carry out reacting by heating, follow the tracks of reaction process by a plate and react completely to intermediate 1, termination reaction immediately.Specifically, use the there-necked flask of 2L as the second reaction vessel.Meanwhile, select the potassium phthalimide of the intermediate 1,120g of 130g, the content of DMF is 500 ml, is heated to 80 DEG C of reactions 30 minutes.
Subsequently, be cooled to 80 DEG C, the reaction solution of acquisition be poured into water and stir.After filtration, obtain fluffy solid.Dry after washing, by ethyl alcohol recrystallization, the intermediate 2 of white needle-like crystals can be obtained.In this layoutprocedure, reaction solution is poured in 2000mlL water, stir 5min.Bake out temperature is 70-80 DEG C, by the ethyl alcohol recrystallization of 500ml.
Then, adopt the there-necked flask of 250ml as the 3rd reaction vessel.In add the ethanol of intermediate 2,300 ml of 30g, by dry-run protection post-heating to 70 DEG C, make intermediate 2 be dissolved completely in ethanol.After waiting for reaction solution cooling, add the hydrazine hydrate of 20g, at the temperature of 80 DEG C, carry out heating reflux reaction 1 hour.Afterwards, stop after the completely dissolve of question response raw material, after carrying out cooling twice to 60 DEG C, add concentrated hydrochloric acid 10 ml, regulate PH to approximate 2.Finally, then carry out heating reflux reaction stopped reaction after 1 hour.
Immediately, be cooled to less than 50 DEG C, add 100 ml water to the reaction solution previously obtained, stir, filter, concentrated filtrate, to no longer flowing out with liquid, adds 500 ml water again, stir, filter, concentrated, can solid be obtained.
Finally, by this dissolution of solid in 100ml ethanol, carry out ice bath and stir 2 hours, cold filtration is realized to 0 DEG C by freeze overnight, rear acquisition white powder solid or white flaky crystals, by drying, design temperature 70-80 DEG C obtains final finished after drying.
" embodiment two "
The preparation method of 2-fluorine ethylamine hydrochloride, it adopts following steps:
First, in the first reaction vessel, put into quantitative 2-fluoroethanol and toluene sulfonyl chloride, carry out reacting by heating after drying protection, stop after completion of the reaction.Specifically, in order to have preferably reaction effect, this first reaction vessel is the there-necked flask of 500ml, and the quantitative factor of the 2-fluoroethanol adopted is 160g.Meanwhile, the quantitative factor of toluene sulfonyl chloride is 190g, and drying tube carries out dry-run protection.The temperature of heating is 120 DEG C, heating reflux reaction 11 hours.After reacting by heating, reacted completely by TLC display checking Tosyl chloride.
Afterwards, carry out the recovery of 2-fluoroethanol, blast the rare gas element of such as nitrogen etc. by distillation, blowout HCl gas, obtains mesosome 1 through distillation.Specifically, the distillation temperature of employing is 40 DEG C, and underpressure distillation adopts 20 mmHg, carries out at 142 DEG C.Further, distillation temperature is good with 60 DEG C.
Then, add intermediate 1, potassium phthalimide, DMF in the second reaction vessel after, carry out reacting by heating, follow the tracks of reaction process by a plate and react completely to intermediate 1, termination reaction immediately.Specifically, use the there-necked flask of 2L as the second reaction vessel.Meanwhile, select the potassium phthalimide of the intermediate 1,130g of 160g, the content of DMF is 1600ml, is heated to 120 DEG C of reactions 45 minutes.
Subsequently, be cooled to 80 DEG C, the reaction solution of acquisition be poured into water and stir.Hold over night, after to be filtered, obtains fluffy solid.Dry after washing, by ethyl alcohol recrystallization, the intermediate 2 of white needle-like crystals can be obtained.In this layoutprocedure, reaction solution is poured in 2000mlL water, stir 5min.Bake out temperature is 70-80 DEG C, by the ethyl alcohol recrystallization of 500ml.
Then, adopt the there-necked flask of 250ml to add the intermediate 2 of 60g, the ethanol of 500ml in this embodiment as the 3rd reaction vessel, by dry-run protection post-heating to 80 DEG C, make intermediate 2 be dissolved completely in ethanol.After waiting for reaction solution cooling, add the hydrazine hydrate of 20g, at the temperature of 80 DEG C, carry out heating reflux reaction 1 hour.Afterwards, stop after the completely dissolve of question response raw material, after carrying out cooling twice to 60 DEG C, add concentrated hydrochloric acid 10 ml, regulate PH to approximate 2.Finally, then carry out heating reflux reaction stopped reaction after 1 hour.
Immediately, less than 50 DEG C are cooled to the reaction solution previously obtained, add 200 ml water, agitation and filtration, concentrated filtrate, again add 800 ml water, stir, to be filtered, concentrated, can solid be obtained.
Finally, by this dissolution of solid in 200ml ethanol, carry out ice bath and stir 2 hours, filter, rear acquisition white powder solid or white flaky crystals, by drying, design temperature 70-80 DEG C obtains final finished after drying.
Can be found out by above-mentioned character express, after adopting the present invention, optimize technique and reclaim, improve overall yield.Meanwhile, can adopt the hydrogen chloride gas in conventional nitrogen eliminating reaction solution, what avoid extraction waits operation, removes the employing of extraction from.Further, optimize the overall reaction times, improve plant factor.What is more important, by ethanol and water extraction impurity removing technology, the product content not only obtained high (99%), and yield improves, and both not only cost of material is cheap, be easy to get, pollution-free.Thus, while minimizing cost, the output of final thing is significantly increased.
Claims (9)
- The preparation method of 1.2-fluorine ethylamine hydrochloride, is characterized in that comprising the following steps:1. step, puts into quantitative 2-fluoroethanol and toluene sulfonyl chloride in the first reaction vessel, carries out reacting by heating, stop after completion of the reaction after drying protection;2. step, carries out the recovery of 2-fluoroethanol by distillation, import rare gas element, blowout HCl gas, then obtains mesosome 1 through underpressure distillation;3. step, carries out reacting by heating after adding intermediate 1, potassium phthalimide, DMF in the second reaction vessel, follows the tracks of reaction process and reacts completely to intermediate 1, termination reaction immediately by thin-layer chromatography (TLC) plate point plate;4., carry out being cooled to 80 DEG C to 90 DEG C, reaction solution step 3. obtained is poured into water and stirs step, carry out freeze overnight afterwards, after to be filtered, obtain fluffy solid, dry after washing, by ethyl alcohol recrystallization, obtain the intermediate 2 of white needle-like crystals;Step 5., intermediate 2, ethanol is added in the 3rd reaction vessel, by heating after dry-run protection, intermediate 2 is made to be dissolved completely in ethanol, after waiting for reaction solution cooling, add hydrazine hydrate, carry out heating reflux reaction, stop after the completely dissolve of question response raw material, after carrying out cooling twice, carry out PH adjustment, then carry out stopped reaction after heating reflux reaction;6. step, cools the reaction solution that 5. step obtains, adds water, stirs cooling, filters, and distillation filtrate is flowed out to no longer including liquid, again adds water, stirs, again filter, underpressure distillation, obtain solid;7., dissolution of solid step 6. obtained in ethanol, carries out ice bath stirring to step, obtains white powder solid or white flaky crystals, after super-dry, obtain final finished after cold filtration.
- 2. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1; it is characterized in that: described step 1. in; first reaction vessel is the there-necked flask of 500ml; the quantitative factor of described 2-fluoroethanol is 130 to 160g; the quantitative factor of described toluene sulfonyl chloride is 160 to 190g; described dry-run protection is realized by drying tube protection, and described heat-processed is employing 90 to 120 DEG C of heating reflux reactions 5 to 11 hours.
- 3. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, is characterized in that: described step 1. in, after reacting by heating, by TLC plate display checking Tosyl chloride react completely.
- 4. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, is characterized in that: the 2. described distillation temperature of step is 40 to 70 DEG C, then carries out the decompression steaming phase, and described underpressure distillation employing 10 to 20 mmHg, carry out at 135 to 142 DEG C.
- 5. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, it is characterized in that: step 3. described in the second reaction vessel be the there-necked flask of 2L, the content of intermediate 1 is 130 to 160g, the content of potassium phthalimide is 120 to 130g, the content of DMF is 500 to 1600ml, is heated to 80 to 120 DEG C of reactions 30 to 45 minutes.
- 6. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, it is characterized in that: the 4. described reaction solution of step is poured in 2000 to 3000mL water, stir 5-150 min, then in 5 to 20 DEG C of quiet hold over night of temperature be, bake out temperature is 70 to 80 DEG C, by the ethyl alcohol recrystallization of 500 to 800ml.
- 7. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, it is characterized in that: described step 5. in, 3rd reaction vessel is the there-necked flask of 250ml, the amount adding intermediate 2 is 30 to 60g, the ethanol adopted is 300 to 500ml, dry-run protection is carried out by drying tube, be heated to 70 to 80 DEG C, add hydrazine hydrate 20 to 30g, be heated to 80 to 81 DEG C of back flow reaction about 1 to 2 hour, by the completely dissolve of TLC plate detection reaction raw material, then stopped reaction, after question response liquid is cooled to 60 DEG C, add concentrated hydrochloric acid 10 to 30ml, regulate PH to 2, back flow reaction stopped reaction after 1 to 2 hour again.
- 8. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, it is characterized in that: described step 6. in, less than 50 DEG C are cooled to, after adding 100 to 200ml water to the reaction solution that 5. step obtains, stir 2 h, then cross filtering, following concentrated filtrate, again add 500 to 800ml water, stir 2h, cross filtering, following concentrated filtrate, obtains solid.
- 9. the preparation method of 2-fluorine ethylamine hydrochloride according to claim 1, is characterized in that: described step 7. in, adopt ethyl alcohol recrystallization obtain, then dry obtain product.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112645822A (en) * | 2020-12-09 | 2021-04-13 | 苏州金蚕新材料科技有限公司 | Preparation method of 2-fluoroethylamine hydrochloride |
| CN113045477A (en) * | 2019-12-26 | 2021-06-29 | 中蓝晨光化工研究设计院有限公司 | Preparation method of fluorine-containing primary amine intermediate |
| CN114014784A (en) * | 2021-12-10 | 2022-02-08 | 许昌学院 | Novel chiral or achiral monofluoroethylamine compounds, preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4030994A (en) * | 1971-06-18 | 1977-06-21 | Merck & Co., Inc. | Substitutive fluorination of organic compounds |
-
2014
- 2014-11-10 CN CN201410626808.0A patent/CN104496825B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4030994A (en) * | 1971-06-18 | 1977-06-21 | Merck & Co., Inc. | Substitutive fluorination of organic compounds |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113045477A (en) * | 2019-12-26 | 2021-06-29 | 中蓝晨光化工研究设计院有限公司 | Preparation method of fluorine-containing primary amine intermediate |
| CN113045477B (en) * | 2019-12-26 | 2022-11-01 | 中蓝晨光化工研究设计院有限公司 | Preparation method of fluorine-containing primary amine intermediate |
| CN112645822A (en) * | 2020-12-09 | 2021-04-13 | 苏州金蚕新材料科技有限公司 | Preparation method of 2-fluoroethylamine hydrochloride |
| CN112645822B (en) * | 2020-12-09 | 2022-06-07 | 苏州当量生物医药有限公司 | Preparation method of 2-fluoroethylamine hydrochloride |
| CN114014784A (en) * | 2021-12-10 | 2022-02-08 | 许昌学院 | Novel chiral or achiral monofluoroethylamine compounds, preparation method and application |
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