CN107216256A - A kind of synthetic method of N, N diisopropyl ethylenediamine - Google Patents
A kind of synthetic method of N, N diisopropyl ethylenediamine Download PDFInfo
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- CN107216256A CN107216256A CN201710357099.4A CN201710357099A CN107216256A CN 107216256 A CN107216256 A CN 107216256A CN 201710357099 A CN201710357099 A CN 201710357099A CN 107216256 A CN107216256 A CN 107216256A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Abstract
The invention discloses a kind of N, the synthetic method of N diisopropyl ethylenediamines, using diisopropylamine and chloroacetonitrile as initiation material, through aminolysis reaction and the step of reduction reaction two synthesis N, N diisopropyl ethylenediamines, present invention process route is advanced, rationally, raw material is cheap and easily-available, and reaction condition is gentle for process conditions, safety simple to operate, Atom economy is high, and production cost is low, and the three wastes are small, it is suitable for industrialized production, with larger implementary value and economic results in society.
Description
Technical field
The present invention relates to a kind of synthesis of organic compound, more particularly to a kind of N, the synthesis side of N- diisopropyl ethylenediamines
Method.
Background technology
N, N- diisopropyl ethylenediamine are the key intermediates for synthesizing the medicines such as pramiracetam.Pramiracetam belongs to pyrrolidines
Ketone cereboactive drug, its English entitled Pramiracetam, chemical entitled N- [2- (N, N- diisopropyl) ethyl] -2- oxygen -1- pyrroles
Alkyl acetamide is coughed up, molecular formula is C14H27N3O2.Pramiracetam is a kind of efficient, the understanding activator of low toxicity, tolerance well, is fitted
For the elderly's notice and memory disorder, benign aging is forgetful, the prevention and treatment of Alzheimer's, by the U.S.
Warner-Lambert is developed, and the synthesis of pramiracetam is generally with ring butyrolactam, chloracetyl chloride or ethyl chloroacetate and N, N-
Diisopropyl ethylenediamine is raw material, occurs intramolecular condensation and is made.
N as can be seen here, N- diisopropyl ethylenediamines are the key intermediates for synthesizing pramiracetam.Therefore, development technology road
Line is advanced, and rationally, raw material is cheap and easily-available, the N of reaction condition temperature for process conditions, and N- diisopropyl ethylenediamines synthesis technique has weight
The meaning wanted.
At present, the N of domestic and foreign literature report, the synthetic method of N- diisopropyl ethylenediamines has following 4 kinds：
Method one：Gabriel methods
This method be synthesis N, traditional method of N- diisopropyl ethylenediamines, it with 1,2- Bromofumes be initiation material,
Synthesized with phthalimide and obtain N- (2- bromoethyls) phthalimide, tried afterwards by nucleophilic of diisopropylamine
Agent, reaction obtains N- [(N, N- diisopropylaminoethyl)] ethyl phthalimide, and it is different that finally hydrolysis obtains product N, N- bis-
Propyl group ethylenediamine.
Because the volume of nucleophile diisopropylamine is larger, steric hindrance effect is unfavorable for reaction and carried out, and to enter in tube sealing
OK, severe reaction conditions.Although Peng Zhenyun etc. [Xuzhou Medical College's journal, 1999,19 (40), 273-274] is carried out to the method
Improve, yield increases, but total recovery also only reaches 50% or so.
Method two：Ammoniation process
Li Maolin etc. [applied chemistry, 2005,22 (12), 1384-1386] is reported using diisopropylamine as raw material, first with ring
Ring-opening reaction occurs for oxidative ethane, and N, N- diisopropyl ethylenediamines then is made through chlorination, aminating reaction.
The method yield is higher, but thionyl chloride consumption is big, produces a large amount of tail gas, and processing is difficult, pollutes environment；And ammonification is anti-
It should need to carry out under elevated pressure conditions, it is higher to equipment requirement.
Method three：Aziridine open loop method
Dong Yanfei etc. [chemical industry and engineering, 2007,24 (4), 367-369] report using 2- ethylaminoethanols as raw material first
Synthesize aziridine, then with diisopropylamine ring-opening reaction, synthesize target product N, N- diisopropyl ethylenediamine.
The method yield is higher, but all needs to carry out at high temperature per single step reaction, high energy consumption；Alchlor is used in reaction,
Wastewater flow rate is big, difficult, pollutes environment.
Method four：Catalytic hydrogenation method
Japan Patent JP05025098 reports N, and N- diisopropylaminoethyl second eyeballs are bored under catalysis in thunder Buddhist nun, and high-pressure hydrogenation obtains N,
N- diisopropyl ethylenediamines.
The method high income, but the preparation of raw material N, N- diisopropylaminoethyl second eyeball need to use potassium cyanide, and its toxicity is big, production peace
Full property is low；Secondly catalyst thunder Buddhist nun's cobalt is expensive, and reaction need to be carried out under 9~10MPa high pressure.
For problem above, the present invention proposes a kind of novel N, N- diisopropyl ethylenediamine synthesis techniques, this method tool
There is raw material to be easy to get, reaction condition is gentle, simple to operate, there is no particular/special requirement to equipment, Atom economy is high, and course of reaction meets
The advantages of Green Chemistry is required, is extremely suitable for industrialized production.
The content of the invention：
For problems of the prior art, the present invention provides a kind of low cost, high income, environment-friendly N, N- bis-
Isopropyl ethylenediamine synthetic method.
To achieve the above objectives, the present invention is realized by such technical scheme：Using diisopropylamine and chloroacetonitrile as
Initiation material, N, N- diisopropyl ethylenediamines are synthesized through aminolysis reaction and the step of reduction reaction two.
The synthetic method of a kind of N, N- diisopropyl ethylenediamine, it is characterised in that described method is：(1) aminolysis reaction：
Using diisopropylamine and chloroacetonitrile as raw material, under the conditions of alkali-free or alkali, in solvent stir, be heated to 40~130 DEG C reaction 4~
48h, after reaction terminates, N, N- diisopropylaminoethyl acetonitriles is made in reaction solution post processing；The alkali be sodium hydroxide, potassium hydroxide,
Sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus；The solvent is Cl~C10Organic solvent；(2) reduction reaction：With step
(1) N made from, N- diisopropylaminoethyl acetonitrile are raw material, under reducing agent and catalysts conditions, stir, are heated in solvent
25~130 DEG C of 2~36h of reaction, after reaction terminates, reacting liquid filtering distills after organic layer concentration, collects 169~172 DEG C and evaporate
Point, N, N- diisopropyl ethylenediamines is made；Described reducing agent is potassium borohydride, sodium borohydride, Lithium Aluminium Hydride, sodium sulfite；
Described catalyst is Raney's nickel, nickel chloride, cobalt chloride, palladium carbon；The solvent is water or Cl~C10Organic solvent.
Alkali described in described step (1) is preferable over sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, bicarbonate
Sodium, saleratus, more preferably in sodium carbonate or potassium carbonate.
Reaction dissolvent described in described step (1) be preferable over methanol, ethanol, isopropanol, acetonitrile, ethyl acetate, benzene,
Toluene, dichloromethane, chloroform, more preferably in benzene or toluene.
The ratio between amount for the material that feeds intake of chloroacetonitrile and diisopropylamine and alkali described in described step (1) is 1：1~5：
0.01~2, preferably 1：1.5~2：1.1~1.3；The volumetric usage of described solvent is calculated as 5 with diisopropylamine quality~
25mL/g, preferably 6~10mL/g.
Reaction temperature described in described step (1) is preferably 70~95 DEG C, and the reaction time is preferably 5~8h.
Reducing agent described in described step (2) is preferable over sodium borohydride, potassium borohydride, even Lithium Aluminium Hydride, two sulfurous
Sour sodium, sodium sulfite, more preferably in sodium borohydride or potassium borohydride.
Catalyst described in described step (2) is preferable over Raney's nickel, nickel chloride, cobalt chloride, palladium carbon, more preferably in thunder
Buddhist nun's nickel.
Reaction dissolvent described in described step (2) is preferable over tetrahydrofuran, methanol, ethanol, benzene, toluene, more preferably
In methanol or ethanol.
N in described step (2), the ratio between N- diisopropylaminoethyls acetonitrile and the amount for the material that feeds intake of reducing agent and catalyst are
1：1~2.5：0.01~0.2, preferably 1：1.1~1.5：0.05~0.1；The volumetric usage of described solvent is with N, and N- bis- is different
Third aminoacetonitriles quality is calculated as 8~30mL/g, preferably 10~15mL/g.
Compared with prior art, there is this method raw material to be easy to get, and reaction condition is gentle, simple to operate, to equipment without spy
Different to require, Atom economy is high, and course of reaction meets the advantages of Green Chemistry is required, is extremely suitable for industrialized production.
Embodiment
With reference to specific embodiment, the present invention is described further
Embodiment 1
Aminolysis reaction：In 500ml three-necked flask, chloroacetonitrile 37.25g (0.5mol) is added, potassium carbonate 69g is added
Diisopropylamine 55.55g (0.55mol) is added dropwise in (0.5mol), toluene 200ml, and control rate of addition makes system temperature unobvious
Rise, completion of dropping is warming up to 100 DEG C and continues to react 5h, and reaction is crossed after terminating and filters out insoluble matter, is concentrated under reduced pressure except solvent obtains N,
N- diisopropylaminoethyl acetonitrile 58.4g, colourless liquid, yield 83.4%.
Embodiment 2
Aminolysis reaction：In 1000ml three-necked flask, chloroacetonitrile 37.25g (0.5mol) is added, potassium carbonate 69g is added
Diisopropylamine 55.55g (0.55mol) is added dropwise in (0.5mol), ethanol 500ml, and control rate of addition makes system temperature unobvious
Rise, completion of dropping is warming up to 60 DEG C and continues to react 15h, and reaction filters out insoluble matter after terminating, is concentrated under reduced pressure except solvent obtains N,
N- diisopropylaminoethyl acetonitrile 46.2g, colourless liquid, yield 66%.
Embodiment 3
Aminolysis reaction：In 500ml three-necked flask, chloroacetonitrile 37.25g (0.5mol) is added, diisopropylamine is added dropwise
202g (2mol), control rate of addition makes system temperature substantially not rise, and completion of dropping is warming up to 84 DEG C and continues to react 16h,
Reaction end is concentrated under reduced pressure to obtain N, N- diisopropylaminoethyl acetonitrile 38.8g, colourless liquid, yield 55.4%.
Embodiment 4
Aminolysis reaction：In 1000ml three-necked flask, chloroacetonitrile 75g (1mol) is added, sodium carbonate 127.2g is added
Diisopropylamine 106.05g (1.05mol) is added dropwise in (1.2mol), chloroform 500ml, and control rate of addition does not have system temperature
There is obvious rising, completion of dropping is warming up to 60 DEG C and continues to react 16h, and reaction is crossed after terminating and filters out insoluble matter, is concentrated under reduced pressure except molten
Agent obtains N, N- diisopropylaminoethyl acetonitrile 98.5g, colourless liquid, yield 70.3%.
Embodiment 5
Aminolysis reaction：In 500ml three-necked flask, chloroacetonitrile 37.25g (0.5mol) is added, sodium acid carbonate 84g is added
Diisopropylamine 55.55g (0.55mol) is added dropwise in (1mol), tetrahydrofuran 250ml, and control rate of addition makes system temperature not bright
Aobvious to rise, completion of dropping is warming up to 65 DEG C and continues to react 15h, and reaction is crossed after terminating and filters out insoluble matter, is concentrated under reduced pressure except solvent is obtained
N, N- diisopropylaminoethyl acetonitrile 42.8g, colourless liquid, yield 61.1%.
Embodiment 6
Reduction reaction：In 1000ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 70g (0.5mol), methanol are added
400ml, Raney's nickel 0.05mol, ice-water bath make the temperature of system be less than 5 DEG C, and sodium borohydride 28.5g is slowly added in batches
(0.75mol), control temperature is not higher than 15 DEG C, and charging is warmed to room temperature continuation and stirs 1h naturally after finishing, then heat to 60 DEG C
8h is reacted, filtering and concentrating collects 169~172 DEG C of cuts, obtain N, N- diisopropyl ethylenediamine 59.1g, nothing to dry rear air-distillation
Color liquid, yield 82.1%, gas phase purity 98.2%.
Embodiment 7
Reduction reaction：In 1000ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 70g (0.5mol), methanol are added
400ml, Raney's nickel 0.025mol, ice-water bath make the temperature of system be less than 5 DEG C, and sodium borohydride 28.5g is slowly added in batches
(0.75mol), control temperature is not higher than 15 DEG C, and charging is warmed to room temperature continuation and stirs 1h naturally after finishing, then heat to 60 DEG C
8h is reacted, filtering and concentrating collects 169~172 DEG C of cuts, obtain N, N- diisopropyl ethylenediamine 52.4g, nothing to dry rear air-distillation
Color liquid, yield 72.8%, gas phase purity 98.1%.
Embodiment 8
Reduction reaction：In 1000ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 70g (0.5mol), toluene are added
300ml, cobalt chloride 0.05mol, ice-water bath make the temperature of system be less than 5 DEG C, and sodium borohydride 28.5g is slowly added in batches
(0.75mol), control temperature is not higher than 15 DEG C, and charging is warmed to room temperature continuation and stirs 1h naturally after finishing, then heat to 100 DEG C
6h is reacted, filtering and concentrating collects 169~172 DEG C of cuts, obtain N, N- diisopropyl ethylenediamine 46.8g, nothing to dry rear air-distillation
Color liquid, yield 65%, gas phase purity 97.9%.
Embodiment 9
Reduction reaction：In 1000ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 70g (0.5mol), tetrahydrochysene are added
Furans 500ml, ice-water bath makes the temperature of system be less than 5 DEG C, and Lithium Aluminium Hydride 28g (0.7mol), nickel chloride are slowly added in batches
0.01mol, controls temperature to be not higher than 15 DEG C, charging is warmed to room temperature continuation and stirs 1h naturally after finishing, and then heats to 65 DEG C instead
5h is answered, add water stirring, filtering and concentrating collects 169~172 DEG C of cuts, obtain N, N- diisopropyl ethylenediamines to dry rear air-distillation
60.3g, colourless liquid, yield 83.7%, gas phase purity 98.4%.
Embodiment 10
Reduction reaction：In 500ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 35g (0.25mol), benzene are added
200ml, cobalt chloride 0.02mol, ice-water bath make the temperature of system be less than 5 DEG C, and potassium borohydride 27g is slowly added in batches
(0.5mol), controls temperature to be not higher than 15 DEG C, charging is warmed to room temperature continuation and stirs 1h naturally after finishing, and then heats to 80 DEG C instead
Answer 7h, filtering and concentrating collects 169~172 DEG C of cuts to air-distillation after dry, obtain N, N- diisopropyl ethylenediamines 21.1g is colourless
Liquid, yield 58.6%, gas phase purity 97.4%.
Embodiment 11
Reduction reaction：In 500ml three-necked flask, N, N- diisopropylaminoethyl acetonitrile 35g (0.25mol), ethanol are added
250ml, palladium carbon 0.015mol, ice-water bath make the temperature of system be less than 5 DEG C, and sodium borohydride 19g (0.5mol) is slowly added in batches,
Control temperature is not higher than 15 DEG C, and charging is warmed to room temperature continuation and stirs 1h naturally after finishing, and then heats to 78 DEG C of reaction 6h, filtering
Rear air-distillation is concentrated to dryness, 169~172 DEG C of cuts is collected, obtains N, N- diisopropyl ethylenediamine 23.5g, colourless liquid, yield
65.3%, gas phase purity 98.5%.
Claims (8)
1. the synthetic method of a kind of N, N- diisopropyl ethylenediamine, it is characterised in that described method is：(1) aminolysis reaction：With
Diisopropylamine and chloroacetonitrile are raw material, under the conditions of alkali-free or alkali, are stirred in solvent, be heated to 40~130 DEG C of reactions 4~
48h, after reaction terminates, N, N- diisopropylaminoethyl acetonitriles is made in reaction solution post processing；The alkali be sodium hydroxide, potassium hydroxide,
Sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus；The solvent is Cl~C10Organic solvent；(2) reduction reaction：With step
(1) N made from, N- diisopropylaminoethyl acetonitrile are raw material, under reducing agent and catalysts conditions, stir, are heated in solvent
25~130 DEG C of 2~36h of reaction, after reaction terminates, reacting liquid filtering distills after organic layer concentration, collects 169~172 DEG C and evaporate
Point, N, N- diisopropyl ethylenediamines is made；Described reducing agent is potassium borohydride, sodium borohydride, Lithium Aluminium Hydride, sodium sulfite；
Described catalyst is Raney's nickel, nickel chloride, cobalt chloride, palladium carbon；The solvent is water or Cl~C10Organic solvent.
2. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly the alkali in (1) selects any one in sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acid carbonate, saleratus.
3. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly in (1) in reaction dissolvent selection methanol, ethanol, isopropanol, acetonitrile, ethyl acetate, benzene, toluene, dichloromethane, chloroform
Any one.
4. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly the ratio between chloroacetonitrile and diisopropylamine described in (1) and the amount for the material that feeds intake of alkali are 1：1~5：0.01~2；Described is molten
The volumetric usage of agent is calculated as 5~25mL/g with chloroacetonitrile quality.
5. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly the reducing agent in (2) selects any one in sodium borohydride, potassium borohydride, Lithium Aluminium Hydride, sodium dithionite, sodium sulfite
Kind.
6. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly any one in the catalyst choice Raney's nickel in (2), nickel chloride, cobalt chloride, palladium carbon.
7. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that：Described step
Suddenly the reaction dissolvent in (2) selects any one in tetrahydrofuran, methanol, ethanol, benzene, toluene.
8. a kind of N according to claim 1, the synthetic method of N- diisopropyl ethylenediamines, it is characterised in that described step
Suddenly N in (2), the ratio between N- diisopropylaminoethyls acetonitrile and the amount for the material that feeds intake of reducing agent and catalyst are 1：1~2.5：0.01~
0.2；The volumetric usage of described solvent is calculated as 8~30mL/g with N, N- diisopropylaminoethyl acetonitrile quality.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066221A (en) * | 2019-05-16 | 2019-07-30 | 海门瑞一医药科技有限公司 | A kind of preparation method of cyclopropyl-methylamine |
| CN115141104A (en) * | 2022-06-29 | 2022-10-04 | 万华化学集团股份有限公司 | Environment-friendly organic amine and preparation method and application thereof |
| CN115991653A (en) * | 2022-12-12 | 2023-04-21 | 河南省三生药业有限公司 | Preparation method of prazoracetam key intermediate N, N-diisopropyl ethylenediamine |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0525098A (en) * | 1991-07-19 | 1993-02-02 | Koei Chem Co Ltd | Production of n,n-di-substituted ethylenediamine |
| JP2003176261A (en) * | 2001-10-05 | 2003-06-24 | Showa Denko Kk | Method for producing aminoacetonitrile and glycine derivative |
| CN1810766A (en) * | 2006-01-04 | 2006-08-02 | 四川大学 | Nitrile reducing process to prepare amine |
| CN1810765A (en) * | 2006-01-04 | 2006-08-02 | 四川大学 | Reduction of nitrile in nickel chloride/potassium borohydride reduction system to prepare amine |
| CN102786421A (en) * | 2012-08-15 | 2012-11-21 | 中国科学院深圳先进技术研究院 | Method of preparing integral generation polypropyleneimine dendrimer by reducing cyano group |
| CN103709043A (en) * | 2013-12-12 | 2014-04-09 | 南京工业大学 | Method for preparing 2-(4-chlorophenyl)ethylamine |
| CN104557561A (en) * | 2014-12-15 | 2015-04-29 | 北京悦康科创医药科技有限公司 | Method for preparing N1,N1-diisoprylamino ethylamine or salts of N1,N1-diisoprylamino ethylamine |
-
2017
- 2017-05-19 CN CN201710357099.4A patent/CN107216256B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0525098A (en) * | 1991-07-19 | 1993-02-02 | Koei Chem Co Ltd | Production of n,n-di-substituted ethylenediamine |
| JP2003176261A (en) * | 2001-10-05 | 2003-06-24 | Showa Denko Kk | Method for producing aminoacetonitrile and glycine derivative |
| CN1810766A (en) * | 2006-01-04 | 2006-08-02 | 四川大学 | Nitrile reducing process to prepare amine |
| CN1810765A (en) * | 2006-01-04 | 2006-08-02 | 四川大学 | Reduction of nitrile in nickel chloride/potassium borohydride reduction system to prepare amine |
| CN102786421A (en) * | 2012-08-15 | 2012-11-21 | 中国科学院深圳先进技术研究院 | Method of preparing integral generation polypropyleneimine dendrimer by reducing cyano group |
| CN103709043A (en) * | 2013-12-12 | 2014-04-09 | 南京工业大学 | Method for preparing 2-(4-chlorophenyl)ethylamine |
| CN104557561A (en) * | 2014-12-15 | 2015-04-29 | 北京悦康科创医药科技有限公司 | Method for preparing N1,N1-diisoprylamino ethylamine or salts of N1,N1-diisoprylamino ethylamine |
Non-Patent Citations (3)
| Title |
|---|
| CHIBA, TOSHIRO ETAL: "Anodic cyanation of tertiary aliphatic and heterocyclic amines", 《JOURNAL OF ORGANIC CHEMISTRY 》 * |
| IBANEZ CATALAN, J.: "Synthesis of O-[1-(m-trifluoromethylphenyl)indazol-3-yl]-N-(dialkylaminoalkyl)-2-hydroxy amides", 《ANALES DE QUIMICA (1968-1979)》 * |
| SHUNSUKE KOTANI ETAL: "A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters", 《EUR. J. ORG. CHEM.》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066221A (en) * | 2019-05-16 | 2019-07-30 | 海门瑞一医药科技有限公司 | A kind of preparation method of cyclopropyl-methylamine |
| CN110066221B (en) * | 2019-05-16 | 2022-03-08 | 海门瑞一医药科技有限公司 | Preparation method of cyclopropylmethylamine |
| CN115141104A (en) * | 2022-06-29 | 2022-10-04 | 万华化学集团股份有限公司 | Environment-friendly organic amine and preparation method and application thereof |
| CN115991653A (en) * | 2022-12-12 | 2023-04-21 | 河南省三生药业有限公司 | Preparation method of prazoracetam key intermediate N, N-diisopropyl ethylenediamine |
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