CN107827764A - A kind of preparation method of double β amino ketones or double β amino esters - Google Patents
A kind of preparation method of double β amino ketones or double β amino esters Download PDFInfo
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- CN107827764A CN107827764A CN201711206400.8A CN201711206400A CN107827764A CN 107827764 A CN107827764 A CN 107827764A CN 201711206400 A CN201711206400 A CN 201711206400A CN 107827764 A CN107827764 A CN 107827764A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention discloses a kind of double β amino ketones or the preparation method of double β amino esters compounds.After it is by the way that beta diketone or β ketone esters and diamine compound are mixed in proportion, catalyst monoethanolamine acetate ion liquid is added, 3 6h of reaction are stirred at room temperature, after reaction terminates, filters and purifying obtains.The catalyst recoverable that filtrate in the present invention obtains through extracting liquid separation.The beneficial effects of the present invention are：Catalyst is easily prepared, and pollution is small, and without using solvent in reaction, preparation process is simple to operate, and post-reaction treatment is simple, environmental protection.The high income of product, can reach 70~88%.
Description
Technical field
The present invention relates to the preparation method of a kind of double beta-amino ketones or double beta-amino esters, belong to technical field of organic synthesis.
Background technology
Ionic liquid (ionic liquid, abbreviation IL) is each by the world as " cleaning " solvent and new catalyst system and catalyzing
State is catalyzed the receiving and concern on boundary and petroleum chemical enterprise circle.
Beta-amino ketones or beta-amino ester are a kind of important bioactive substances, have cough-relieving, antibacterial, anti-inflammatory anticancer, anti-
The multiple biological activities such as virus, calm, analgesic, decompression, suppression oedema, anticoagulation.This kind of compound is synthesized more using load
Solid acid is as catalyst, and costly, preparation process is more complicated for most of catalyst, it is difficult to recycles and is easy to environment
Pollution.
The content of the invention
The technical problems to be solved by the invention be to provide it is a kind of with it is inexpensive, environmental pollution is small, easily prepared and recovery
By the use of ionic liquid as catalyst, catalyze and synthesize double beta-amino ketones or the novel preparation method of double beta-amino esters.The present invention
Method is simple, product yield high.
The technical solution adopted by the present invention is specifically described as follows.
The preparation method of a kind of double beta-amino ketones or double beta-amino ester type compounds, with beta-diketon or 'beta '-ketoester and two aminations
Compound is raw material, and using monoethanolamine acetate ion liquid as catalyst, reaction 3-6h is stirred at room temperature, after reaction terminates, filters, is pure
Change, obtain corresponding double beta-amino ketones or double beta-amino ester type compounds.
In the present invention, the structure of beta-diketon and 'beta '-ketoester is respectively as shown in Formula II and formula III：
Wherein：R2Selected from C1~C8It is any in alkyl, phenyl or substituted-phenyl；R3Selected from C1~C6Alkyl is any.
In the present invention, R2Selected from methyl, 3- phenyl, 4- phenyl is any in 5- phenyl or 4- methyl；R3For methyl or second
Base；
In the present invention, the structure of diamine compound is shown in formula I：
Wherein：R1 is-CH2-) n- or C6H4-, wherein n=2,3,4,5；M=1,2.
In the present invention, R1 is-CH2CH2-,-CH2CH2CH2-,-C6H4-, or-C6H4C6H4-。
In the present invention, catalyst amount is the 15%~22% of diamine compound molal quantity.
In the present invention, purifying uses means re-crystallization, and recrystallization solvent for use is absolute ethyl alcohol.
In the present invention, isometric ethyl acetate and water are added in the filtrate after recrystallization, after being layered, by the liquid in water layer
After body concentration and recovery, monoethanolamine acetate ion liquid is obtained, as catalyst recycling.
In the present invention, monoethanolamine acetate ion liquid is made up of monoethanolamine quaternary ammonium cation with acetic acid anion.
In the present invention, using beta-diketon as raw material, the reaction equation of the preparation method of double beta-amino ketones is as follows：
Compared to the prior art, the beneficial effects of the present invention are：
Catalyst monoethanolamine acetate ion liquid used is to be in a liquid state at normal temperatures in the preparation process of the present invention, by
Monoethanolamine quaternary ammonium cation and acetic acid anion composition.There is ionic liquid acid and heat endurance, steam to force down, easily
Prepare, pollution is small, and course of reaction is simple to operate, without using solvent, while avoids the H with severe corrosive2SO4Deng locating after reaction
Reason is simple, environmental protection.The high income of product, can reach 70~88%.
Brief description of the drawings
Fig. 1 is acetylacetone,2,4-pentanedione contracting Isosorbide-5-Nitrae-phenylenediamine that embodiment 1 obtains1HNMR schemes.
Fig. 2 is the bis-acetylacetonate contracting benzidine that embodiment 2 obtains1HNMR schemes.
Embodiment
The present invention is described in further detail below by specific embodiment, but is not intended to limit the present invention.
Embodiment 1
A kind of preparation method of double beta-amino ketones acetylacetone,2,4-pentanedione contracting Isosorbide-5-Nitrae-phenylenediamines, comprises the following steps：
(1) 2.5mmol acetylacetone,2,4-pentanediones, are put into 25mL round-bottomed flask, 1mmol Isosorbide-5-Nitraes-phenylenediamine, are shaken up；
(2), add again into round-bottomed flask 0.2mmol ionic liquid ethanol amine acetate (self-control, preparation method referring to
Victor HA,Silvana M,Manuel MP,Martin A,Miguel I(2011)J Chem Thermodyn 43:
997) reaction 3h, is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain sterling levulinic with absolute ethyl alcohol
Ketone contracting Isosorbide-5-Nitrae-phenylenediamine；Total recovery is 75%, mp.114.3~115.2 DEG C；5mL water and 5mL acetic acid second are successively added in filtrate
Ester, after liquid layered, by the monoethanolamine acetate ion liquid concentration recycling (rate of recovery, 99%) in water layer.
Using Buker AM-500 (500M) NMR, using TMS as internal standard, CDCl3For solvent.Fig. 1 is embodiment 1
Nuclear magnetic spectrum figure, the nuclear-magnetism modal data for surveying product is as follows：1H NMR(500MHz,CDCl3)δ:12.57 (s, 2H, N-H),
7.58-7.56 (d, 4H, Ar-H), 7.21-7.19 (d, 4H, Ar-H), 5.24 (s, 2H, CH=), 2.14 (s, 6H, CH3), 2.08
(s, 6H, CH3).Proof product is acetylacetone,2,4-pentanedione contracting Isosorbide-5-Nitrae-phenylenediamine.
Embodiment 2
A kind of preparation method of double beta-amino ketones bis-acetylacetonate contracting benzidine, comprises the following steps：
(1) 2.5mmol acetylacetone,2,4-pentanediones, are put into 25mL round-bottomed flask, 1mmol benzidine, are shaken up；
(2) 0.2mmol ionic liquid ethanol amine acetates, are added into round-bottomed flask again, reaction 4h is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain sterling biacetyl with absolute ethyl alcohol
Acetone contracting benzidine；Total recovery is 78%, mp.115.0~116.8 DEG C；5mL water and 5mL ethyl acetate are successively added in filtrate,
After liquid layered, by the monoethanolamine acetate ion liquid concentration recycling in water layer；Using Buker AM-500
(500M) NMR, using TMS as internal standard, CDCl3For solvent.Fig. 2 is the nuclear magnetic spectrum figure of embodiment 2, surveys product
Nuclear-magnetism modal data is as follows：δ：12.57 (2H, s, N-H), 7.58-7.56 (4H, d, Ar-H), 7.21-7.19 (4H, d, Ar-H),
5.24 (2H, s, CH=), 2.14 (6H, s, CH3), 2.08 (6H, s, CH3) to prove product be bis-acetylacetonate contracting benzidine.
Embodiment 3
A kind of preparation method of double 1- phenyl -1, the 3- diacetyl contracting ethylenediamines of double beta-amino ketones, comprises the following steps：
(1), it is put into 2.5mmol 1- phenyl -1,3- diacetyl in 25mL round-bottomed flask, 1mmol ethylenediamines,
Shake up；
(2) 0.2mmol ionic liquid ethanol amine acetates, are added into round-bottomed flask again, reaction 5h is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain the double 1- benzene of sterling with absolute ethyl alcohol
Base -1,3- diacetyl contracting ethylenediamines；Total recovery is 82%, mp.182.7~182.9 DEG C；Water and acetic acid second are successively added in filtrate
Ester, after liquid layered, by the monoethanolamine acetate ion liquid concentration recycling in water layer；Using Buker AM-500
(500M) NMR, using TMS as internal standard, CDCl3For solvent.The nuclear-magnetism modal data of surveyed product is as follows：δ：11.579 (s,
2H, N-H), 7.88-7.87 (d, 4H, Ar-H), 7.44-7.42 (m, 6H, Ar-H), 5.73 (s, 2H, CH=), 3.61-3.60
(t, 4H, J=3HZ, CH2-), 2.097 (s, 6H, CH3-).It is double 1- phenyl -1,3- diacetyl contracting ethylenediamines to prove product.
Embodiment 4
A kind of preparation method of double 1- phenyl -1, the 3- diacetyl contracting propane diamine of double beta-amino ketones, comprises the following steps：
(1) 2.5mmol1- phenyl -1,3- diacetyl, is put into 25mL round-bottomed flask, 1mmol propane diamine, is shaken
It is even；
(2) 0.2mmol ionic liquid ethanol amine acetates, are added into round-bottomed flask again, reaction 3h is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain the double 1- benzene of sterling with absolute ethyl alcohol
Base -1,3- diacetyl contracting propane diamine；Total recovery is 76%, mp.86.0~88.8 DEG C；5mL water and 5mL second are successively added in filtrate
Acetoacetic ester, after liquid layered, by the monoethanolamine acetate ion liquid concentration recycling in water layer；Using Buker
AM-500 (500M) NMR, using TMS as internal standard, CDCl3For solvent.The nuclear-magnetism modal data of surveyed product is as follows：δ：
11.55 (s, 2H, N-H), 7.88-7.87 (d, 4H, Ar-H), 7.45-7.41 (m, 6H, Ar-H), 5.73 (s, 2H, CH=),
3.54-3.53 (m, 4H, J=3HZ, CH2-), 2.12 (s, 6H, CH3-), 2.06-2.04 (m, 2H, CH2-).Prove that product is double
1- phenyl -1,3- diacetyl contracting propane diamine.
Embodiment 5
A kind of preparation method of bis-acetylacetonate contracting ethylenediamine, comprises the following steps：
(1) 2.5mmol acetylacetone,2,4-pentanediones, are put into 25mL round-bottomed flask, 1mmol ethylenediamines, are shaken up；
(2) 0.2mmol ionic liquid ethanol amine acetates, are added into round-bottomed flask again, reaction 3h is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain sterling biacetyl with absolute ethyl alcohol
Acetone contracting ethylenediamine；Total recovery is 88%, mp.110.2~110.5 DEG C；5mL water and 5mL ethyl acetate are successively added in filtrate,
After liquid layered, by the monoethanolamine acetate ion liquid concentration recycling in water layer；Using Buker AM-500
(500M) NMR, using TMS as internal standard, CDCl3For solvent.The nuclear-magnetism modal data of surveyed product is as follows：δ：10.916
(2H, s, N-H), 5.018 (2H, s, CH=), 3.450-3.438 (4H, t, CH2-), 2.023 (6H, s, CH3-), 1.929 (6H,
S, CH3-) to prove product be bis-acetylacetonate contracting ethylenediamine.
Embodiment 6
A kind of preparation method of diacetyl acetate methyl esters contracting ethylenediamine, comprises the following steps：
(1) 2.5mmol methyl acetoacetates, are put into 25mL round-bottomed flask, 1mmol ethylenediamines, are shaken up；
(2) 0.2mmol ionic liquid ethanol amine acetates, are added into round-bottomed flask again, reaction 6h is stirred at room temperature；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain sterling biacetyl with absolute ethyl alcohol
Methyl acetate contracting ethylenediamine；Total recovery is 70%, mp.137.2~137.5 DEG C；Water and ethyl acetate are successively added in filtrate, is treated
After liquid layered, by the monoethanolamine acetate ion liquid concentration recycling in water layer；Using Buker AM-500
(500M) NMR, using TMS as internal standard, CDCl3For solvent.The nuclear-magnetism modal data of surveyed product is as follows：δ：8.65(2H,
S, N-H), 4.52 (2H, s, CH=), 3.64 (6H, s, CH3-), 3.39-3.38 (4H, m, CH2-), 1.94 (6H, s, CH3-).Card
Bright product is diacetyl acetate methyl esters contracting ethylenediamine.
Embodiment 7
The monoethanolamine acetate ion liquid of recovery is used in embodiment 1 as catalyst, a kind of double beta-amino ketones levulinics
The preparation method of ketone contracting Isosorbide-5-Nitrae-phenylenediamine, comprises the following steps：
(1) 2.5mmol acetylacetone,2,4-pentanediones, are put into 25mL round-bottomed flask, 1mmol Isosorbide-5-Nitraes-phenylenediamine, are shaken up；
(2) the ionic liquid ethanol amine acetate reclaimed, is added in embodiment 1 into round-bottomed flask again, is stirred at room temperature anti-
Answer 3h；
(3) after, step (2) reaction terminates, crude product is filtered to obtain, crude product recrystallizes to obtain sterling levulinic with absolute ethyl alcohol
Ketone contracting Isosorbide-5-Nitrae-phenylenediamine, yield 74.8%, mp.114.3~115.2 DEG C；5mL water and 5mL ethyl acetate are successively added in filtrate,
After liquid layered, the monoethanolamine acetate ion liquid concentration recycling in water layer recycles three times, yield base
This holding is constant, and average yield is 75% or so.
Above-mentioned specific embodiment is used only to illustrate the present invention, rather than limits the invention, in the present invention
Spirit and claims in, to any modifications and changes for making of the present invention, both fall within the protection model of the present invention
Enclose.
Claims (9)
1. the preparation method of a kind of double beta-amino ketones or double beta-amino ester type compounds, it is characterised in that with beta-diketon or β -one
Ester and diamine compound are raw material, using monoethanolamine acetate ion liquid as catalyst, reaction 3-6h are stirred at room temperature, reaction terminates
Afterwards, filter, purify, obtain corresponding double beta-amino ketones or double beta-amino ester type compounds.
2. preparation method according to claim 1, it is characterised in that the structure of beta-diketon and 'beta '-ketoester respectively such as Formula II and
Shown in formula III：
Wherein：R2Selected from C1~C8It is any in alkyl, phenyl or substituted-phenyl；R3Selected from C1~C6Alkyl is any.
3. preparation method according to claim 1, it is characterised in that R2Selected from methyl, 3- phenyl, 4- phenyl, 5- phenyl or
It is any in 4- methyl；R3For methyl or ethyl.
4. preparation method according to claim 1, it is characterised in that the structure of diamine compound is shown in formula I：
Wherein：R1 is-CH2-) n- or C6H4-, wherein n=2,3,4,5；M=1,2.
5. preparation method according to claim 1, it is characterised in that R1 is selected from-CH2CH2-,-CH2CH2CH2-,-C6H4-,
Or-C6H4C6H4-。
6. preparation method according to claim 1, it is characterised in that catalyst amount is diamine compound molal quantity
15%~22%.
7. preparation method according to claim 1, it is characterised in that purify and use means re-crystallization, it is molten used in recrystallization
Agent is absolute ethyl alcohol.
8. preparation method according to claim 7, it is characterised in that isometric acetic acid second is added in the filtrate after recrystallization
Ester and water, after being layered, after the liquid concentration recovery in water layer, monoethanolamine acetate ion liquid is obtained, as catalyst
Recycle.
9. preparation method according to claim 1, it is characterised in that monoethanolamine acetate ion liquid is by monoethanolamine season
Ammonium cation forms with acetic acid anion.
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Cited By (3)
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| CN113582934A (en) * | 2021-08-02 | 2021-11-02 | 昆明理工大学 | Preparation method and application of Pentane metal-free homogeneous catalyst |
| WO2023116940A1 (en) * | 2021-12-22 | 2023-06-29 | 苏州大学 | MODIFICATION METHOD FOR PRECURSOR OF β-KETOIMINE LIGAND, AND PRODUCT THEREOF |
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