CN105503624A - Preparation method of 2-hydroxyl-3-butene-1-amine - Google Patents
Preparation method of 2-hydroxyl-3-butene-1-amine Download PDFInfo
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- CN105503624A CN105503624A CN201610040086.XA CN201610040086A CN105503624A CN 105503624 A CN105503624 A CN 105503624A CN 201610040086 A CN201610040086 A CN 201610040086A CN 105503624 A CN105503624 A CN 105503624A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
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Abstract
The invention discloses a preparation method of 2-hydroxyl-3-butene-1-amine. The preparation method comprises the following specific steps: (1) taking acrolein as a start raw material to react with trimethylsilyl cyanide at room temperature in the presence of lithium perchlorate trihydrate to obtain 2-hydroxyl-3-butene-1-nitrile; (2) with diethyl ether or tetrahydrofuran as a solvent, reducing the 2-hydroxyl-3-butene-1-nitrile with lithium aluminum hydride to obtain a crude product of 2-hydroxyl-3-butene-1-amine; (3) making the crude product of 2-hydroxyl-3-butene-1-amine react with hydrochloric acid to obtain 2-hydroxyl-3-butene-1-amine hydrochloride; and (4) making the 2-hydroxyl-3-butene-1-amine hydrochloride react with alkali to finally obtain the 2-hydroxyl-3-butene-1-amine. According to the method disclosed by the invention, without a trimethylsilyl protection group removal process, the operation of reduced pressure distillation is avoided, the reaction path is shortened, and the operation is simple.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly, relate to a kind of preparation method of 2-hydroxyl-3-butene-1-amine.
Background technology
2-hydroxyl-3-butene-1-amine is a kind of important chemical intermediate be all widely used in fields such as medicine, agricultural chemicals, and its structural formula is such as formula shown in (1).
Chemical synthesis process at present about it has following four kinds.
Route one (J.Am.Chem.Soc.1950,72,4792), its reaction equation is such as formula shown in (2):
It adopts 3,4-epoxy-1-butylene and ammoniacal liquor are raw material, but the regioselectivity of this synthetic route ammonia solution is low, and target product 2-hydroxyl-3-butene-1-amine that reaction generates is difficult to be separated with by product 2-amino-3-butene-1-ol, cause aftertreatment inconvenience, and reaction yield is also low.
Route two (J.Heterocycl.Chem.1990,27,811-812), nineteen ninety, Gardrat etc. improve the method for synthesis 2-hydroxyl-3-butene-1-amine, and its reaction equation is such as formula shown in (3).
It generates by the addition reaction of propenal and trimethylammonium nitrile silane the crotononitrile containing TMS protecting group, and productive rate is 90%, then itrile group reduces and takes off TMS protecting group further, and then obtains 2-hydroxyl-3-butene-1-amine, and productive rate is 56%.Production process is more loaded down with trivial details, time consumption longer.
Route three (Chemico-BiologicalInteractions2007,166,104-111 and Chem.Res.Toxicol.2010,23,118-133), its reaction equation is such as formula shown in (4):
This route overcomes the low problem of route one regioselectivity.This route and route two similar; all reduce by addition, itrile group and take off TMS protecting group three-step reaction to prepare 2-hydroxyl-3-butene-1-amine; the method of final employing underpressure distillation carries out separation and purification, thus obtains the higher 2-hydroxyl-3-butene-1-amine of purity.This route and the difference of route two are that the reagent of used de-TMS protecting group is different, and namely adopt mineral alkali NaOH to instead of organic bases trolamine, reduce further reaction cost, simultaneous reactions yield also increases, and brings up to 59.4% from 56%.
Route four (ZL2013.10337936.9), its reaction equation is such as formula shown in (5):
This route and route two, three similar, be all by addition, itrile group reduction and take off TMS protecting group three-step reaction and prepare 2-hydroxyl-3-butene-1-amine.This route is different from route two and is that the way of purification of 2-hydroxyl-3-butene-1-amine is different with route three part, namely adopts amine substance salify, and then uses base extraction amine salt, and then obtain highly purified 2-hydroxyl-3-butene-1-amine.
In the building-up process of route two, three, four, all need the process through de-TMS protecting group, such route is more loaded down with trivial details, and workload is comparatively large, consuming time longer.
Summary of the invention
In order to overcome the deficiencies in the prior art, the object of this invention is to provide a kind of preparation method not adopting protecting group just can obtain 2-hydroxyl-3-butene-1-amine simply, efficiently.
Technical scheme of the present invention is specifically described as follows.
The invention provides a kind of preparation method of 2-hydroxyl-3-butene-1-amine, concrete steps are as follows:
(1) be first starting raw material with propenal, when three water lithium perchlorates exist and trimethylsilyl cyanide react to obtain 2-hydroxyl-3-butene-1-nitrile;
(2) with ether or tetrahydrofuran (THF) for solvent, 2-hydroxyl-3-butene-1-nitrile obtains the thick product of 2-hydroxyl-3-butene-1-amine through Lithium Aluminium Hydride reduction;
(3) the thick product of 2-hydroxyl-3-butene-1-amine of above-mentioned gained and hydrochloric acid are reacted, obtain 2-hydroxyl-3-butene-1-amine hydrochlorate;
(4) the 2-hydroxyl-3-butene-1-amine hydrochlorate of above-mentioned gained and alkali are reacted, finally obtain 2-hydroxyl-3-butene-1-amine;
The reaction equation of preparation 2-hydroxyl-3-butene-1-amine is as follows:
In above-mentioned steps (1), the mol ratio of propenal, trimethylsilyl cyanide and three water lithium perchlorates is 1:(1.4-1.6): (1-1.1).
In above-mentioned steps (2), the mol ratio of 2-hydroxyl-3-butene-1-nitrile and tetrahydrochysene lithium aluminium is 1:2 ~ 1:8.
In above-mentioned steps (3), the concentration of hydrochloric acid is between 10-37%, and in the thick product of 2-hydroxyl-3-butene-1-amine and hydrochloric acid, the mol ratio of HCl is between 1:3 ~ 1:15.
In above-mentioned steps (4), the mol ratio of 2-hydroxyl-3-butene-1-amine hydrochlorate and alkali is 1:2 ~ 1:5.Preferably, alkali is sodium hydroxide or potassium hydroxide.
The preparation method of a kind of 2-hydroxyl-3-butene-1-amine provided by the invention, concrete steps are as follows:
(1) in reaction vessel, add propenal, trimethylsilyl cyanide and three water lithium perchlorates, stir lower reaction, by TLC monitoring reaction, after reaction terminates, add ethyl acetate, solids removed by filtration, the saturated common salt water washing of gained organic phase, anhydrous Na
2sO
4after drying, rotary evaporation obtains 2-hydroxyl-3-butene-1-nitrile;
(2) solvent and Lithium Aluminium Hydride is added to filling being equipped with in the reaction vessel of condensing reflux pipe of 2-hydroxyl-3-butene-1-nitrile, be heated to 40-60 DEG C under stirring and carry out back flow reaction, TLC monitors reaction, and reaction terminates rear stopping back flow reaction, reaction solution is cooled to room temperature, obtains reaction solution; Again under agitation in add Na
2sO
412H
2o and ether, leave standstill 5-120min by reaction solution, after rotary evaporation boils off ether under supernatant liquid room temperature, obtains the thick product of 2-hydroxyl-3-butene-1-amine;
(3) in the thick product of 2-hydroxyl-3-butene-1-amine of step (2) gained, hydrochloric acid is added, stir lower room temperature reaction 10-15h, ether is added in reaction solution, static layering, upper organic phase is removed, lower floor's aqueous phase rotary evaporation removes moisture content, and the white solid obtained is 2-hydroxyl-3-butene-1-amine hydrochlorate;
(4) in the 2-hydroxyl-3-butene-1-amine hydrochlorate of step (3) gained, alkali aqueous solution and ether is added, static layering, collects upper organic phase, dry, rotary evaporation removes the colourless liquid that ether obtains, and is 2-hydroxyl-3-butene-1-amine.
Beneficial effect of the present invention is as follows:
The preparation method of a kind of 2-hydroxyl-3-butene-1-amine of the present invention; adopt propenal, trimethylsilyl cyanide and three water lithium perchlorates under the condition not having reaction solvent, directly obtain 2-hydroxyl-3-butene-1-nitrile in preparation process; do not need through de-trimethyl silicane protecting group process; reaction scheme is shortened, simple to operate.
Further, the preparation method of a kind of 2-hydroxyl-3-butene-1-amine of the present invention, its preparation process is at ambient temperature, reacted by propenal, trimethylsilyl cyanide and three water lithium perchlorates, in short period of time just can high yield obtain 2-hydroxyl-3-butene-1-nitrile, and do not add reaction solvent in reaction process; The higher 2-hydroxyl-3-butene-1-nitrile of purity just can be obtained by simple extraction, washing in last handling process.Simultaneously post-treating method of the present invention, the i.e. method such as acid-base neutralisation, rotary evaporation, one-tenth hydrochloride.Avoid underpressure distillation operation, overcome when the amount of reacting is less, underpressure distillation purification process can not obtain the problem of pure product completely.
In sum, the preparation method of a kind of 2-hydroxyl-3-butene-1-amine of the present invention, by improving reaction process and condition, has cost lower, simple, convenient, the feature such as short consuming time.
Embodiment
Below by specific embodiment, the present invention is described in further detail, but do not limit the present invention.
Lithium Aluminium Hydride used in various embodiments of the present invention, ether is traditional Chinese medicines reagent.
Water circulating pump used in various embodiments of the present invention is: Shanghai Yu Kang circulates multiplex vacuum pump SHB-IIIA;
Agitator is: Mei Ying Pu, Shanghai MYPII-2 constant temperature blender with magnetic force; Rotary Evaporators: Shanghai Yu Kang Rotary Evaporators W.S206B.
Embodiment 1
A preparation method for 2-hydroxyl-3-butene-1-amine, specifically comprises the following steps:
(1) in reactor, propenal (1.12g is added successively, 0.02mol), trimethylsilyl cyanide (2.98g, 0.03mol) He three water lithium perchlorate (3.21g, 0.02mol), controlling mixing speed is react under 500r/min room temperature condition, by after starting raw material propenal completely dissolve used in TLC monitoring reaction in reaction process, adds ethyl acetate, solids removed by filtration, the saturated common salt water washing three times of gained organic phase, anhydrous Na
2sO
4after drying, rotary evaporation obtains 2-hydroxyl-3-butene-1-nitrile.
In above-mentioned TLC monitoring reaction course, developping agent used is sherwood oil: ether=7:1;
The propenal that above-mentioned reaction is used: trimethylsilyl cyanide: three water lithium perchlorates are 1mol:1.5mol:1mol;
(2) in the there-necked flask that condensing reflux pipe is housed, add the Lithium Aluminium Hydride (1.56g that purity is greater than 97% successively, 0.04mol), anhydrous diethyl ether (5ml) and 2-hydroxyl-3-butene-1-nitrile (1.55g, 0.01mol), controlling mixing speed is be heated to 45 DEG C under 1000r/min to carry out back flow reaction, by after starting raw material 2-hydroxyl-3-butene-1-nitrile completely dissolve used in TLC monitoring reaction in back flow reaction process, stop back flow reaction, reaction solution is cooled to room temperature, obtains reaction solution.
In above-mentioned TLC monitoring reaction course, developping agent used is sherwood oil: ether=5:1;
2-hydroxyl-3-butene-1-nitrile that above-mentioned back flow reaction is used: Lithium Aluminium Hydride: ether is 1mol:4mol:500ml;
(3) under agitation in the reaction solution of step (2) gained, 7.5gNa is added respectively
2sO
412H
2o and 33ml ether, reaction solution is left standstill 20min, collect supernatant liquid, supernatant liquid is poured in 100 milliliters of single port bottles, the bath temperature controlling Rotary Evaporators is room temperature, rotating speed is 100r.p.m, and Rotary Evaporators connects the water circulating pump that Shanghai Yu Kang produces, and is then placed in by single port bottle and Rotary Evaporators evaporates ether obtains the thick product of 0.01mol2-hydroxyl-3-butene-1-amine;
Above-mentioned Na used
2sO
412H
2the amount of O and ether, by 2-hydroxyl-3-butene-1-nitrile: Na
2sO
412H
2o: ether is 1mol:2.1mol:3300ml;
(4) in the thick product of 2-hydroxyl-3-butene-1-amine of the 0.01mol of step (3) gained, 10ml3mol/L hydrochloric acid is added, controlling mixing speed under room temperature is that 500r/min carries out reaction 48h, 10ml ether is added in the reaction solution of gained, separating funnel is used to carry out static layering, upper organic phase is removed, lower floor's aqueous phase is poured in 100 milliliters of single port bottles, the bath temperature controlling Rotary Evaporators is room temperature, rotating speed is 100r.p.m, Rotary Evaporators connects the 2562C-50 dry type piston pump of Welch, then single port bottle is placed on Rotary Evaporators and namely obtains 0.80g white solid after evaporative removal moisture content, i.e. 2-hydroxyl-3-butene-1-amine hydrochlorate,
Calculate in molar ratio, the thick product of 2-hydroxyl-3-butene-1-amine that above-mentioned reaction process is used: 3mol/L hydrochloric acid is 1:3;
(5) in single port bottle, add the 0.80g2-hydroxyl-3-butene-1-amine hydrochlorate of step (4) gained successively, 13.3ml mass percent concentration is the NaOH aqueous solution and the 10ml ether of 15%, shake by separating funnel separatory after 5min, upper organic phase anhydrous Na
2sO
4drying, rotary evaporation removes the colourless liquid that ether obtains, i.e. the 2-hydroxyl-3-butene-1-amine of 0.55g;
Calculate in molar ratio, the 2-hydroxyl-3-butene-1-amine hydrochlorate of the trimethyl silicane protection that above-mentioned reaction process is used: mass percent concentration is the NaOH aqueous solution of 15%: ether is 1mol:5mol:1000ml.
The nuclear-magnetism detected result of the colourless liquid of above-mentioned gained is as follows:
1HNMR(500MHz,CDCl
3):δ2.03-2.06(m,3H),3.18-3.25(m,1H),3.55-3.61(s,1H),4.27-4.32(m,1H),5.21-5.26(m,1H)，5.38-5.40(m,1H)，5.85-5.90(m,1H)。
The above results shows, the colourless liquid of preparation method's gained of a kind of 2-hydroxyl-3-butene-1-amine of the present invention is 2-hydroxyl-3-butene-1-amine.
Embodiment 2
A preparation method for 2-hydroxyl-3-butene-1-amine, specifically comprises the following steps:
(1) in reactor, propenal (1.12g is added successively, 0.02mol), trimethylsilyl cyanide (2.98g, 0.03mol) He three water lithium perchlorate (6.42g, 0.04mol), controlling mixing speed is react under 700r/min room temperature condition, by after starting raw material propenal completely dissolve used in TLC monitoring reaction in reaction process, adds ethyl acetate, solids removed by filtration, the saturated common salt water washing three times of gained organic phase, anhydrous Na
2sO
4after drying, rotary evaporation obtains 2-hydroxyl-3-butene-1-nitrile.
In above-mentioned TLC monitoring reaction course, developping agent used is sherwood oil: ether=7:1;
The propenal that above-mentioned reaction is used: trimethylsilyl cyanide: three water lithium perchlorates are 1mol:1.5mol:2mol;
(2) in the there-necked flask that condensing reflux pipe is housed, add the Lithium Aluminium Hydride (0.78g that purity is greater than 97% successively, 0.02mol), anhydrous diethyl ether (5ml) and 2-hydroxyl-3-butene-1-nitrile (1.55g, 0.01mol), controlling mixing speed is be heated to 50 DEG C under 500r/min to carry out back flow reaction, by after starting raw material 2-hydroxyl-3-butene-1-nitrile completely dissolve used in TLC monitoring reaction in back flow reaction process, stop back flow reaction, reaction solution is cooled to room temperature, obtains reaction solution.
In above-mentioned TLC monitoring reaction course, developping agent used is sherwood oil: ether=5:1;
2-hydroxyl-3-butene-1-nitrile that above-mentioned back flow reaction is used: Lithium Aluminium Hydride: ether is 1mol:2mol:500ml;
(3) under agitation in the reaction solution of step (2) gained, 15gNa is added respectively
2sO
412H
2o and 66ml ether, reaction solution is left standstill 20min, collect supernatant liquid, supernatant liquid is poured in 100 milliliters of single port bottles, the bath temperature controlling Rotary Evaporators is room temperature, rotating speed is 100r.p.m, and Rotary Evaporators connects the water circulating pump that Shanghai Yu Kang produces, and is then placed in by single port bottle on Rotary Evaporators and evaporates the thick product of 2-hydroxyl-3-butene-1-amine that ether obtains the protection of 0.01mol trimethyl silicane;
Above-mentioned Na used
2sO
412H
2the amount of O and ether, the 2-hydroxyl-3-butene-1-nitrile by trimethyl silicane protection: Na
2sO
412H
2o: ether is 1mol:2.1mol:3300ml;
(4) 20ml3mol/L hydrochloric acid is added in the thick product of 2-hydroxyl-3-butene-1-amine protected to the trimethyl silicane of the 0.01mol of step (3) gained, controlling mixing speed under room temperature is that 500r/min carries out reaction 48h, stopped reaction, 10ml ether is added in the reaction solution of gained, separating funnel is used to carry out static layering, upper organic phase is removed, lower floor's aqueous phase is poured in 100 milliliters of single port bottles, the bath temperature controlling Rotary Evaporators is room temperature, rotating speed is 100r.p.m, Rotary Evaporators connects the 2562C-50 dry type piston pump of Welch, then single port bottle is placed on Rotary Evaporators and namely obtains 1.60g white solid after evaporative removal moisture content, i.e. 2-hydroxyl-3-butene-1-amine hydrochlorate,
Calculate in molar ratio, the thick product of 2-hydroxyl-3-butene-1-amine of the trimethyl silicane protection that above-mentioned reaction process is used: 3mol/L hydrochloric acid is 1:3;
(5) in single port bottle, add the 1.60g2-hydroxyl-3-butene-1-amine hydrochlorate of step (4) gained successively, 26.6ml mass percent concentration is the NaOH aqueous solution and the 20ml ether of 15%, shake by separating funnel separatory after 5min, upper organic phase anhydrous Na
2sO
4drying, rotary evaporation removes the colourless liquid that ether obtains, i.e. the 2-hydroxyl-3-butene-1-amine of 1.10g;
Calculate in molar ratio, the 2-hydroxyl-3-butene-1-amine hydrochlorate of the trimethyl silicane protection that above-mentioned reaction process is used: mass percent concentration is the NaOH aqueous solution of 15%: ether is 1mol:5mol:1000ml.
Claims (7)
1. a preparation method for 2-hydroxyl-3-butene-1-amine, it is characterized in that, concrete steps are as follows:
(1) be first starting raw material with propenal, when three water lithium perchlorates exist and trimethylsilyl cyanide room temperature reaction obtain 2-hydroxyl-3-butene-1-nitrile;
(2) with ether or tetrahydrofuran (THF) for solvent, 2-hydroxyl-3-butene-1-nitrile obtains the thick product of 2-hydroxyl-3-butene-1-amine through Lithium Aluminium Hydride reduction;
(3) the thick product of 2-hydroxyl-3-butene-1-amine of step (2) gained and hydrochloric acid are reacted, obtain 2-hydroxyl-3-butene-1-amine hydrochlorate;
(4) the 2-hydroxyl-3-butene-1-amine hydrochlorate of step (3) gained and alkali are reacted, finally obtain 2-hydroxyl-3-butene-1-amine;
The reaction equation of preparation 2-hydroxyl-3-butene-1-amine is as follows:
2. preparation method as claimed in claim 1, it is characterized in that, in step (1), the mol ratio of propenal, trimethylsilyl cyanide and three water lithium perchlorates is 1:(1.4-1.6): (1-2).
3. preparation method as claimed in claim 1, it is characterized in that, in step (2), the mol ratio of 2-hydroxyl-3-butene-1-nitrile and tetrahydrochysene lithium aluminium is 1:2 ~ 1:8.
4. preparation method as claimed in claim 1, is characterized in that, in step (3), the concentration of hydrochloric acid is between 10-37%, and in the thick product of 2-hydroxyl-3-butene-1-amine and hydrochloric acid, the mol ratio of HCl is between 1:3 ~ 1:15.
5. preparation method as claimed in claim 1, it is characterized in that, in step (4), the mol ratio of 2-hydroxyl-3-butene-1-amine hydrochlorate and alkali is 1:2 ~ 1:5.
6. preparation method as claimed in claim 1, it is characterized in that, described alkali is sodium hydroxide or potassium hydroxide.
7. the preparation method as described in one of claim 1-6, is characterized in that, concrete steps are as follows:
(1) in reaction vessel, add propenal, trimethylsilyl cyanide and three water lithium perchlorates, stir lower reaction, by TLC monitoring reaction, after reaction terminates, add ethyl acetate, solids removed by filtration, the saturated common salt water washing of gained organic phase, anhydrous Na
2sO
4after drying, rotary evaporation obtains 2-hydroxyl-3-butene-1-nitrile;
(2) solvent and Lithium Aluminium Hydride is added to filling being equipped with in the reaction vessel of condensing reflux pipe of 2-hydroxyl-3-butene-1-nitrile, be heated to 40-60 DEG C under stirring and carry out back flow reaction, TLC monitors reaction, and reaction terminates rear stopping back flow reaction, reaction solution is cooled to room temperature, obtains reaction solution; Again under agitation in add Na
2sO
412H
2o and ether, leave standstill 5-120min by reaction solution, after rotary evaporation boils off ether under supernatant liquid room temperature, obtains the thick product of 2-hydroxyl-3-butene-1-amine;
(3) in the thick product of 2-hydroxyl-3-butene-1-amine of step (2) gained, hydrochloric acid is added, stir lower room temperature reaction 10-15h, ether is added in reaction solution, static layering, upper organic phase is removed, lower floor's aqueous phase rotary evaporation removes moisture content, and the white solid obtained is 2-hydroxyl-3-butene-1-amine hydrochlorate;
(4) in the 2-hydroxyl-3-butene-1-amine hydrochlorate of step (3) gained, alkali aqueous solution and ether is added, static layering, collects upper organic phase, dry, rotary evaporation removes the colourless liquid that ether obtains, and is 2-hydroxyl-3-butene-1-amine.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108658794A (en) * | 2018-06-19 | 2018-10-16 | 界首市创新门窗有限公司 | A kind of green passivator of metal door and window |
| CN108677176A (en) * | 2018-06-19 | 2018-10-19 | 界首市创新门窗有限公司 | A kind of passivation process improving copper window corrosion resistance |
| CN108948441A (en) * | 2018-06-19 | 2018-12-07 | 界首市诚信玩具有限公司 | A kind of natural rubber with excellent machinability |
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| CN108658794A (en) * | 2018-06-19 | 2018-10-16 | 界首市创新门窗有限公司 | A kind of green passivator of metal door and window |
| CN108677176A (en) * | 2018-06-19 | 2018-10-19 | 界首市创新门窗有限公司 | A kind of passivation process improving copper window corrosion resistance |
| CN108948441A (en) * | 2018-06-19 | 2018-12-07 | 界首市诚信玩具有限公司 | A kind of natural rubber with excellent machinability |
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Application publication date: 20160420 |