CN107614478A - The manufacture method of 1 cyclopropylethyI amine or its acid-addition salts - Google Patents
The manufacture method of 1 cyclopropylethyI amine or its acid-addition salts Download PDFInfo
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- CN107614478A CN107614478A CN201680031657.1A CN201680031657A CN107614478A CN 107614478 A CN107614478 A CN 107614478A CN 201680031657 A CN201680031657 A CN 201680031657A CN 107614478 A CN107614478 A CN 107614478A
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- cyclopropylethyi
- acid
- amines
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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
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to the manufacture method of 1 cyclopropylethyI amine or its acid-addition salts.The present invention provides the manufacture cyclopropylethyI amine of high-purity 1 or the method for its acid-addition salts, including：Cyclopropyl, ammonia and hydrogen is set to be reacted in the presence of the Raney nickel being supported on inorganic oxide, in alcohols and/or ethers.
Description
Technical field
The present invention relates to the manufacture of useful the 1- cyclopropylethyI amines or its acid-addition salts of the intermediate as medicine or agricultural chemicals
Method.
Background technology
There is the manufacture method of the fatty amines of cycloalkyl as 1- cyclopropylethyI amines etc, it is known that for example, make
Cyclopropyl (also known as：Cyclopropyl ethyl ketone, acetocyclopropane, cyclopropyl methyl ketone) and ammonia issued in Raney's nickel catalyst
Raw reaction manufactures the method for 1- cyclopropylethyI amines (non-patent literature 1), but Raney's nickel activation method is complicated, and have a spontaneous combustion can
Energy property, its yield are also insufficient.It is also known that manufacture 1- cyclopenta second from cyclopentyl methyl ketone using Leuckart reactions
The method (non-patent literature 2) of base amine, but this method is the reaction under high temperature, and discarded object is also more, and these are in industrial manufacture view
All turn into problem.
As the restoring method carried out using Raney nickel on inorganic oxide is supported on, such as, remember in patent document 1
The method from amine corresponding to the manufacture of (3- oxos butyl) benzene class is carried.But have no knowledge about using it for cyclopropyl
Reduction example.
Prior art literature
Patent document
Patent document 1:Japanese Unexamined Patent Application 63-258444
Non-patent literature
Non-patent literature 1:Zhurnal Organicheskoi Khimii(1976),12,8,1827-1828
Non-patent literature 2:Journal of the American Chemical Society(1954),76,4564-
4567
The content of the invention
The invention problem to be solved
1- cyclopropylethyI amines or its acid-addition salts are useful as the manufacture intermediate of medical agricultural chemicals, pursue energy all the time
It is enough to be manufactured more economically on them in industrial easy and efficient, love environment method.1- rings are obtained using Raney's nickel catalyst
The preparation method of propylethylamine has been known, but generally Raney's nickel needs to use alkali to carry out activation pre-treatment, if dried,
Easily catch fire, so the preparation method is not gratifying as industrial making method.
In addition, cyclopropyl open loop easily by transient metal complex, at this moment commonly known.Therefore exist with after class
Topic：If making to have the compound of cyclopropyl to be reacted in the presence of transient metal complex, accessory substance can be generated and held
Ring body, the separation of the accessory substance and object are not easy.
It is an object of the invention to provide can manufacture high-purity 1- cyclopropyl by easy and efficient, love environment method
The method of ethamine or its acid-addition salts.
The means to solve the problem
The present invention is studied to solve above-mentioned problem, is as a result recognized, can be manufactured height under certain conditions
Purity 1- cyclopropylethyI amines, so as to complete the present invention.
I.e. the present invention relates to make the Raney nickel of cyclopropyl, ammonia and hydrogen on inorganic oxide is supported on
In the presence of, reacted in alcohols and/or ethers and manufacture the method for 1- cyclopropylethyI amines, further relate to by making by party's legal system
The 1- cyclopropylethyI amines and acid produced react in a solvent, to manufacture the method for the acid-addition salts of 1- cyclopropylethyI amines.
Invention effect
The 1- rings third of high-purity can be manufactured in easy and efficient, love environment method by the manufacture method of the present invention
Base ethamine and its acid-addition salts.
Embodiment
In the present invention 1- cyclopropylethyI amines can by it is following like that, make cyclopropyl and ammonia be supported on it is inorganic
React and manufacture in the presence of Raney nickel on oxide.Furthermore there is optical isomer (R bodies and S in 1- cyclopropylethyI amines
Body), here including Isomers and isomer mixture both of these case.
As ammonia, ammonia alcoholic solution, ammonia spirit, liquefied ammonia or ammonia can be used with suitability.As in ammonia alcoholic solution
Alcohol, methanol, ethanol, propyl alcohol, isopropanol, butanol etc. can be included.In the situation using ammonia alcoholic solution, can also double as to be molten
Agent uses.
Ammonia, it is usually used 1~10 times mole, preferably 1~2 times mole relative to 1 mole of cyclopropyl.But
According to reaction condition, the amount outside the scope can also be used sometimes.
As catalyst, the Raney nickel being supported on inorganic oxide is used.As inorganic oxide, can include
Such as diatomite, silica, aluminum oxide, silica, aluminum oxide, magnesia, calcium oxide, titanium oxide, zirconium oxide, oxidation
Niobium, lanthana etc..Wherein preferred diatomite, silica or aluminum oxide, and then preferred diatomite.
The Raney nickel being supported on inorganic oxide, it can use and preferably pass through the usual of the precipitation method or impregnated with method etc
Known method manufacture, commercially available product can also be used, is not particularly limited for the content of the nickel in catalyst.As commercially available
Product, can include for example, wave day catalyst chemical conversion society stabilisation Raney nickel N-103 (diatomite supports, nickel content 52.5
Weight %), the such as the stabilisation nickel SN-750 (diatomite supports, the weight % of nickel content 47) of Sakai chemical industry society
The Raney nickel being supported on inorganic oxide, relative to the weight % of cyclopropyl 100, it is converted into nickel
Content, usually used 1~50 weight %, preferably 5~20 weight %.But according to reaction condition, the model can also be used sometimes
Enclose outer amount.
Hydrogen, relative to cyclopropyl, 1 mole generally preferably uses 1~10 times mole.In addition, pressure is generally selected
From 0.1~10MPa scope, but in order that reaction efficiently carry out, on an industrial scale high-purity, obtain object in high yield,
It is preferred that reacted in the case of keeping pressure certain in the range of 1~10MPa with hydrogen.But according to reaction condition, can also
Use the amount outside the scope, pressure.
The solvent used when in the present invention as manufacture 1- cyclopropylethyI amines, using alcohols and/or ethers, preferably using alcohol
Class.As alcohols, preferably carbon number is 1~6 alcohols, can include such as methanol, ethanol, propyl alcohol, isopropanol, butanol
Deng.In addition, the ethers as ethers, preferably carbon number 1~6, can include such as Anaesthetie Ether, Di Iso Propyl Ether, four
Hydrogen furans, 2- methyltetrahydrofurans, ethylene glycol dimethyl ether etc..Furthermore in the scope for not influenceing reaction, it can also use above-mentioned
Solvent beyond solvent.
The solvent used during 1- cyclopropylethyI amines is manufactured, relative to cyclopropyl usually using 1~20 times of amount (V/
W), preferably 3~15 times amounts (V/W).But according to reaction condition, the amount outside the scope can also be used sometimes.
Reaction temperature, it is typically 80~200 DEG C of degree, preferably 100~130 DEG C of degree, the reaction time is typically 1~12
Hour degree, preferably 1~6 hour degree.
The acid-addition salts of 1- cyclopropylethyI amines, can be by making 1- cyclopropylethyI amines and acid react in a solvent to make
Make.The 1- cyclopropylethyI amines obtained by previous reaction can carry out main reaction in the case where not separating or not purifying.
As the acid-addition salts of the 1- cyclopropylethyI amines manufactured in main reaction, can include with hydrochloric acid, sulfuric acid etc
Inorganic acid or acetic acid etc the salt etc. that is formed of organic acid.
As acid, hydrogen chloride, hydrochloric acid, sulfuric acid, acetic acid etc. can be included.Acid is logical relative to 1 mole of 1- cyclopropylethyI amines
Often use 0.5~5 mole, preferably use 0.5~1.5 mole.But according to reaction condition, the scope can also be used sometimes
Outer amount.
The solvent used when in the present invention as the acid-addition salts for manufacturing 1- cyclopropylethyI amines, is preferably selected from aromatic hydrocarbon
Class, ketone, alcohols and their in the mixed solvent it is one kind or two or more, wherein particularly preferably alcohols and/or aromatic hydrocarbon.Make
To be aromatic hydrocarbon, can include such as benzene,toluene,xylene, chlorobenzene.As ketone, can include such as acetone,
Butanone etc..As the alcohols of alcohols, preferably carbon number 1~6, such as methanol, ethanol, propyl alcohol, isopropanol, fourth can be included
Alcohol etc..
The solvent that uses when manufacturing the acid-addition salts of 1- cyclopropylethyI amines, relative to 1- cyclopropylethyI amines usually using 1~
20 times of amounts (V/W), preferably 3~15 times amounts (V/W).But according to reaction condition, the amount outside the scope can also be used sometimes.
Reaction temperature is usually 0~100 DEG C, is preferably 10~50 DEG C of degree, and the reaction time is usually the journey of 1~10 hour
Degree, the degree of preferably 1~3 hour.
Next, several preferred embodiments of the present invention are included, but the present invention is not limited by them.
【1】A kind of manufacture method of 1- cyclopropylethyI amines or its acid-addition salts, it is characterised in that including：Make cyclopropyl first
Base ketone, ammonia and hydrogen react in the presence of the Raney nickel being supported on inorganic oxide, in alcohols and/or ethers.
【2】Such as【1】Described method, including：
(i) make cyclopropyl, ammonia and hydrogen in the presence of the Raney nickel being supported on inorganic oxide,
Reacted in alcohols and/or ethers, and obtain the 1st process of 1- cyclopropylethyI amines, and
(ii) 1- cyclopropylethyI amines and acid is reacted in a solvent, and obtain the 2nd of the acid-addition salts of 1- cyclopropylethyI amines the
Process.
【3】Such as【1】Or【2】Described method, inorganic oxide are diatomite, silica or aluminum oxide.
【4】Such as【3】Described method, inorganic oxide are diatomite.
【5】Such as【1】~【3】Any one described in method, relative to cyclopropyl, be supported on inorganic oxide
On Raney nickel converted with the content of nickel, have the weight % of 1 weight %~50.
【6】Such as【1】Described method, reacts in alcohols.
【7】Such as【1】~【6】Any one described in method, under 0.1~10MPa pressure with hydrogen react.
【8】Such as【7】Described method, while keeping pressure certain in the range of 1~10MPa, while being reacted with hydrogen.
【9】Such as【1】~【8】Any one described in method, the acid-addition salts of 1- cyclopropylethyI amines are hydrochloride, sulfate
Or acetate.
【10】Such as【2】Described method, as the solvent of the 2nd process, use aromatic hydrocarbon and/or alcohols.
Embodiment
In order to further specifically describe the present invention, following examples are described, but the present invention is not by their limited interpretations.
Dummy suffix notation implication in each table is as follows.
CPMK：Cyclopropyl
CPEA：1- cyclopropylethyI amines
AP：2- aminopentanes (the open loop body as accessory substance)
GC-PA% in each table represents the peak area percentage (Peak area%) obtained by gas-chromatography (GC) analysis,
Its condition determination is as follows.
Pillar:J＆W societies system, DB-1,320 μm of internal diameter, 1.00 μm of thickness, length 30m
Carrier gas:Helium, LGV 23cm/ second
Baking oven:50 DEG C are kept for 12 minutes, and 250 DEG C are warming up to 40 DEG C/min from 50 DEG C, are kept for 3 minutes at 250 DEG C.
Injection port:250 DEG C, split ratio 100:1, bypass flow 123mL/ minutes
Detector:250 DEG C of FID, hydrogen flow rate 40.0mL/ minutes, air velocity 450mL/ minute injection capacities:3.0μ
L
Embodiment 1
By cyclopropyl 20g (purity 99%, 238mmol), 7% methanolic ammonia solution 63.6g (262mmol) and surely
Surely change Raney nickel N-103 (waving catalyst chemical conversion society system day) 1.96g (17.0mmol) to add in 500ml autoclaves, reaction is held
Replaced 2 times with hydrogen in device.Replace backward reaction vessel and fill hydrogen to 2.5MPa, stirred 3 hours at 120 DEG C.Will reaction
Mixture is cooled to 20 DEG C, and it is normal pressure then to make in reaction vessel, filters out insoluble matter.Obtained by being confirmed using gas-chromatography
The reaction of solution carries out rate, and (here, " reaction carries out rate " refers to foregoing CPEA GC-PA%.
Embodiment 2
By cyclopropyl 10g (purity 99%, 119mmol), 7% methanolic ammonia solution 31.8g (131mmol) and surely
Surely change Raney nickel N-103 (waving catalyst chemical conversion society system day) 0.98g (8.5mmol) and add 200ml autoclaves, by reaction vessel
Replaced 2 times with hydrogen.Hydrogen is filled after displacement, to reaction vessel to 2.5MPa, is stirred 3 hours at 100 DEG C.Reaction is mixed
Thing is cooled to 20 DEG C, and it is normal pressure then to make in reaction vessel, filters out insoluble matter.Solution obtained by being confirmed using gas-chromatography
Reaction carry out rate.
Embodiment 3
By cyclopropyl 10g (purity 99%, 119mmol), 7% methanolic ammonia solution 31.8g (131mmol) and surely
Surely change Raney nickel N-103 (waving catalyst chemical conversion society system day) 0.98g (8.5mmol) and add 200ml autoclaves, by reaction vessel
Replaced 2 times with hydrogen.Hydrogen is filled after displacement, to reaction vessel to 3.5MPa, is stirred 3 hours at 120 DEG C.Reaction is mixed
Thing is cooled to 20 DEG C, and it is normal pressure then to make in reaction vessel, filters out insoluble matter.Solution obtained by being confirmed using gas-chromatography
Reaction carry out rate.
Embodiment 4
By cyclopropyl 10g (purity 99%, 119mmol), 7% methanolic ammonia solution 31.8g (131mmol) and surely
Surely change Raney nickel N-103 (waving catalyst chemical conversion society system day) 1.96g (17mmol) and add 200ml autoclaves, by reaction vessel
Replaced 2 times with hydrogen.Replace backward reaction vessel and fill hydrogen to 2.5MPa, stirred 3 hours at 120 DEG C.Reaction is mixed
Thing is cooled to 20 DEG C, and it is normal pressure then to make in reaction vessel, filters out insoluble matter.Solution obtained by being confirmed using gas-chromatography
Reaction carry out rate.
On having recorded starting compound CPMK, object CPEA GC-PA% in the table of embodiment the 1~4, the 1st.
1st table
Comparative example 1
By cyclopropyl 10g (purity 99%, 119mmol), 7% methanolic ammonia solution 31.8g (131mmol) and
10% palladium carbon 1g (0.94mmol) is added in 200ml autoclaves, will be replaced 2 times with hydrogen in reaction vessel.Displacement is backward anti-
Vessel filling hydrogen is answered to be stirred 3 hours at 120 DEG C to 2.5MPa.Reactant mixture is cooled to 20 DEG C, then holds reaction
It is normal pressure in device, filters out insoluble matter.The reaction of solution obtained by being confirmed using gas-chromatography carries out rate.
Comparative example 2
By cyclopropyl 10g (purity 99%, 119mmol), 7% methanolic ammonia solution 31.8g (131mmol) and zinc
1g (15.3mmol) is added to 200ml autoclaves, will be replaced 2 times with hydrogen in reaction vessel.Filled after displacement, to reaction vessel
Hydrogen stirs 3 hours to 2.5MPa at 120 DEG C.Reactant mixture is cooled to 20 DEG C, it is normal then to make in reaction vessel
Pressure, filters out insoluble matter.The reaction of solution obtained by being confirmed using gas-chromatography carries out rate.
On embodiment 1, comparative example 1 and comparative example 2, by starting compound CPMK, object CPEA and accessory substance AP
GC-PA% is documented in the 2nd table.The situation of "-" in CPEA or AP columns represents to be detected with GC.
2nd table
Comparative example 3
By cyclopropyl 20g (purity 99%, 238mmol), 28% ammonia spirit 15.9g (262mmol), water
62.6g (3478mmol) and stabilisation Raney nickel N-103 (waving catalyst chemical conversion society system day) 7.84g (68.2mmol) are added
500ml autoclaves, it will be replaced 2 times with hydrogen in reaction vessel.Hydrogen is filled after displacement, to reaction vessel to 2.0MPa, 120
Stirred 6 hours at DEG C.Reactant mixture is cooled to 20 DEG C, it is normal pressure then to make in reaction vessel, filters out insoluble matter.Use
Gas-chromatography confirms that the reaction of resulting solution carries out rate.
Comparative example 4
By cyclopropyl 20g (purity 99%, 238mmol), 28% ammonia spirit 15.9g (262mmol), toluene
64.0g (694.6mmol) and stabilisation Raney nickel N-103 (waving catalyst chemical conversion society system day) 7.84g (68.2mmol) are added
500ml autoclaves, it will be replaced 2 times with hydrogen in reaction vessel.Hydrogen is filled after displacement, to reaction vessel to 2.0MPa, 120
Stirred 6 hours at DEG C.Reactant mixture is cooled to 20 DEG C, it is normal pressure then to make in reactor, filters out insoluble matter.Use gas
Phase chromatogram confirms that the reaction of resulting solution carries out rate.
On embodiment 1, comparative example 3 and comparative example 4, by starting compound CPMK and object CPEA GC-PA% all
It is documented in the 3rd table.
3rd table
Embodiment 5
1 was used in the reaction except being used as stabilisation Raney nickel N-103 (waving catalyst chemical conversion society system day)
It is other equally to be reacted with previous embodiment 1 beyond secondary, confirm that reaction carries out rate using gas-chromatography.
Embodiment 6
Except as stabilize Raney nickel N-103 (wave day catalyst chemical conversion society system) using be used to for 2 times reacting with
Outside, it is other equally to be reacted with previous embodiment 1, confirm that reaction carries out rate using gas-chromatography.
On embodiment 1, embodiment 5 and embodiment 6, by starting compound CPMK and object CPEA GC-PA% all
It is documented in the 4th table.
4th table
Embodiment 7
Hydrogen chloride gas 13.0g is imported into the methanol solution of the 1- cyclopropylethyI amines obtained according to embodiment 1
(367mmol), it is stirred at room temperature 1 hour, then adds toluene 103.8g (1127mmol).By 95 DEG C at ambient pressure of reactant mixture
Lower distillation for removing methanol, is then cooled to room temperature, separates out crystallization.Dried after crystallization is filtered, obtain 1- cyclopropylethyI amines
Hydrochloride 26.8g (purity 90.6%, yield 84.0%, 183.5 DEG C of fusing point).
1H NMR (solvents：CDCl3/500MHz):δ (ppm)=8.46 (s, 2H), 2.62 (m, 1H), 1.51 (d, 3H),
1.13(m,1H),0.64(m,3H),0.31(m,1H).
Embodiment 8
By cyclopropyl 120g (purity 99%, 1427mmol), methanol 161.4g and stabilize Raney nickel N-
103B (wave day catalyst chemical conversion society system) 11.32g (102.2mmol) adds 900ml autoclaves, from gas cylinder by ammonia (26.73g,
1569mmol) import in reaction vessel.Then will be replaced 2 times with hydrogen in reaction vessel.Hydrogen is filled after displacement, to reaction vessel
Gas stirs to 1.5MPa at 80 DEG C.Pressure in reaction vessel again continues to fill hydrogen to 2.0MPa after lowering,
Stirred 8 hours at 80 DEG C in the case of the pressure in reaction vessel is kept as 2.0MPa.Reactant mixture is cooled to 20 DEG C,
Then it is normal pressure to make in reaction vessel, while with methanol 189.8g agitator treatings while filtering out insoluble matter.Use gas-chromatography
The reaction of solution obtained by confirming carries out rate.
On embodiment 8, starting compound CPMK and object CPEA GC-PA% are documented in the 5th table.
5th table
Embodiment 9
Hydrogen chloride gas 57.2g is imported into the methanol solution of the 1- cyclopropylethyI amines obtained according to embodiment 8
(1569mmol), it is stirred at room temperature 1 hour, then adds toluene 624.2g (6774.9mmol).By reactant mixture at ambient pressure
105 DEG C of distillation for removing methanol, being then cooled to room temperature separates out crystallization.Then filtering for crystallizing is dried, thus obtain 1- cyclopropyl
Ethylamine hydrochloride 158.6g (purity 99.8%, yield 91.4%, 183.5 DEG C of fusing point).
1H NMR (solvents：CDCl3/500MHz):δ (ppm)=8.46 (s, 2H), 2.62 (m, 1H), 1.51 (d, 3H),
1.13(m,1H),0.64(m,3H),0.31(m,1H).
Industry utilizability
By means of the invention it is possible to using cyclopropyl as raw material, high-purity is manufactured under conditions of to industry
1- cyclopropylethyI amines or its acid-addition salts.
Furthermore the specification of the Japanese patent application 2015-117588 proposed on June 10th, 2015, right are wanted
Ask book, accompanying drawing and these all the elements of making a summary all are introduced into this specification and are used as the disclosure of the specification.
Claims (9)
- A kind of 1. manufacture method of 1- cyclopropylethyI amines or its acid-addition salts, it is characterised in that including：Make Cvclopropvlmethvl first Ketone, ammonia and hydrogen react in the presence of the Raney nickel being supported on inorganic oxide, in alcohols and/or ethers.
- 2. the method as described in claim 1, including：(i) make cyclopropyl, ammonia and hydrogen in the presence of the Raney nickel being supported on inorganic oxide, in alcohols And/or reacted in ethers, and the 1st process of 1- cyclopropylethyI amines is obtained, and(ii) 1- cyclopropylethyI amines and acid is reacted in a solvent, and obtain the 2nd process of the acid-addition salts of 1- cyclopropylethyI amines.
- 3. the method as described in claim 1, inorganic oxide is diatomite, silica or aluminum oxide.
- 4. method as claimed in claim 3, inorganic oxide is diatomite.
- 5. the method as described in claim 1, relative to cyclopropyl, the Raney nickel being supported on inorganic oxide Converted with the content of nickel, have the weight % of 1 weight %~50.
- 6. the method as described in claim 1, reacted in alcohols.
- 7. the method as described in claim 1, reacted under 0.1~10MPa pressure with hydrogen.
- 8. method as claimed in claim 7, while keeping pressure certain in the range of 1~10MPa, while anti-with hydrogen Should.
- 9. the method as described in claim 1, the acid-addition salts of 1- cyclopropylethyI amines are hydrochloride, sulfate or acetate.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015117588A JP2018123059A (en) | 2015-06-10 | 2015-06-10 | Method for producing 1-cyclopropyl ethyl amine or salt thereof |
| JP2015-117588 | 2015-06-10 | ||
| PCT/JP2016/066918 WO2016199763A1 (en) | 2015-06-10 | 2016-06-07 | Method for producing 1-cyclopropylethylamine or acid addition salt thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107614478A true CN107614478A (en) | 2018-01-19 |
| CN107614478B CN107614478B (en) | 2020-04-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680031657.1A Active CN107614478B (en) | 2015-06-10 | 2016-06-07 | Process for producing 1-cyclopropylethylamine or acid addition salt thereof |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2018123059A (en) |
| CN (1) | CN107614478B (en) |
| WO (1) | WO2016199763A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63258444A (en) * | 1987-04-15 | 1988-10-25 | Chisso Corp | Production of (3-aminobutyl)benzenes |
| JPH07196586A (en) * | 1993-12-28 | 1995-08-01 | Kuraray Co Ltd | Production of aliphatic diamine |
| US5986141A (en) * | 1998-09-29 | 1999-11-16 | Eastman Chemical Company | Process for the production of cyclopropanemethylamine |
| CN103204811A (en) * | 2006-12-15 | 2013-07-17 | 石原产业株式会社 | Process For Production Of Anthranilamide Compound |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7074805B2 (en) * | 2002-02-20 | 2006-07-11 | Abbott Laboratories | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor |
| TWI435863B (en) * | 2006-03-20 | 2014-05-01 | Nihon Nohyaku Co Ltd | N-2-(hetero) arylethylcarboxamide derivative and pest controlling |
| NL2000613C2 (en) * | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazole pyrazine derivatives. |
-
2015
- 2015-06-10 JP JP2015117588A patent/JP2018123059A/en active Pending
-
2016
- 2016-06-07 WO PCT/JP2016/066918 patent/WO2016199763A1/en active Application Filing
- 2016-06-07 CN CN201680031657.1A patent/CN107614478B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63258444A (en) * | 1987-04-15 | 1988-10-25 | Chisso Corp | Production of (3-aminobutyl)benzenes |
| JPH07196586A (en) * | 1993-12-28 | 1995-08-01 | Kuraray Co Ltd | Production of aliphatic diamine |
| US5986141A (en) * | 1998-09-29 | 1999-11-16 | Eastman Chemical Company | Process for the production of cyclopropanemethylamine |
| CN103204811A (en) * | 2006-12-15 | 2013-07-17 | 石原产业株式会社 | Process For Production Of Anthranilamide Compound |
Non-Patent Citations (1)
| Title |
|---|
| ADROV, P. M. ET AL.: ""ПОЛУЧЕНИЕ (ЦИКЛОПРОПИЛ МЕТИЛ)АМИНОВ ВОССТАНОВИТЕЛЬНЫМ АМИНИРОВАНИЕМ КЕТОНОВ"", 《ZHURNAL ORGANICHESKOI KHIMII》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107614478B (en) | 2020-04-28 |
| WO2016199763A1 (en) | 2016-12-15 |
| JP2018123059A (en) | 2018-08-09 |
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