CN106631824B - Synthesis method of (1-cyclopropyl-1-methyl) ethylamine hydrochloride - Google Patents
Synthesis method of (1-cyclopropyl-1-methyl) ethylamine hydrochloride Download PDFInfo
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- CN106631824B CN106631824B CN201611265611.4A CN201611265611A CN106631824B CN 106631824 B CN106631824 B CN 106631824B CN 201611265611 A CN201611265611 A CN 201611265611A CN 106631824 B CN106631824 B CN 106631824B
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- cyclopropyl
- methyl
- reaction
- ethylamine
- added dropwise
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- FXWZQNRBFXQZCH-UHFFFAOYSA-N 2-cyclopropylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)(N)C1CC1 FXWZQNRBFXQZCH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000001308 synthesis method Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims abstract description 21
- OOXIEUXBOSSXJM-UHFFFAOYSA-N 2-cyclopropylpropan-2-amine Chemical compound CC(C)(N)C1CC1 OOXIEUXBOSSXJM-UHFFFAOYSA-N 0.000 claims abstract description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 17
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims description 22
- 238000010189 synthetic method Methods 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 15
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 11
- -1 1- cyclopropyl Chemical group 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000908 ammonium hydroxide Substances 0.000 claims description 9
- 239000012065 filter cake Substances 0.000 claims description 9
- 238000010791 quenching Methods 0.000 claims description 9
- 230000000171 quenching effect Effects 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 5
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract description 6
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 abstract description 5
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 208000021760 high fever Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/66—Preparation of compounds containing amino groups bound to a carbon skeleton from or via metallo-organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing (1-cyclopropyl-1-methyl) ethylamine hydrochloride. The method comprises the following steps: in an anhydrous tetrahydrofuran solution, cyclopropyl nitrile reacts with methyl lithium and cerium trichloride to generate (1-cyclopropyl-1-methyl) ethylamine; dissolving the crude product of (1-cyclopropyl-1-methyl) ethylamine in ethyl acetate, and then introducing hydrochloric acid gas to react to obtain (1-cyclopropyl-1-methyl) ethylamine hydrochloride. The invention avoids the reaction of sodium azide and ethyl titanate in the prior art, and prepares the (1-cyclopropyl-1-methyl) ethylamine hydrochloride by adopting one-step reaction, thereby improving the yield, lowering the purification difficulty and being easy for large-scale production.
Description
Technical field
The present invention relates to organic chemical industry's intermediate synthesis technical fields, and in particular to a kind of (1- cyclopropyl -1- methyl) second
The synthetic method of base amine hydrochlorate.
Background technique
Low-carbon fatty amine has wide development space in medicine production in pesticide, has become that have large development latent
The specialty industries of power.(1- cyclopropyl -1- methyl) ethylamine is one of low-carbon fatty amine, is a variety of efficient germicides and anti-
The important intermediate of bacterium new drug is widely used in the synthesis of fine chemical product, exploitation (1- cyclopropyl -1- methyl) ethylamine tool
There is biggish social and economic benefit.Synthesis in relation to (1- cyclopropyl -1- methyl) ethylamine, current existing route generally have
It is several below:
Sodium azide is used in the method, meets high fever or strenuous vibration energy violent explosion, and severe toxicity should not operate and amplify.
Tetraethyl titanate is used in the method first step, 28 DEG C of flash-point, is dissolved in ethyl alcohol, benzene, is met water and is extremely easy in decomposition, greatly
Increase operation difficulty, and first step yield is that have 20% or so.The method is also unfavorable for being enlarged.
It can be seen that the synthetic method about (1- cyclopropyl -1- methyl) ethylamine in the prior art, there are raw material valuableness, instead
Answer condition harsh, equipment and control system require stringent, the deficiencies such as total recovery is low, and practical application value is small.
Summary of the invention
The object of the present invention is to provide a kind of synthetic methods of (1- cyclopropyl -1- methyl) ethylamine hydrochloride, solve
The technological deficiency that severe reaction conditions, yield are low in the prior art, should not amplify.
Present invention technical solution used for the above purpose is as follows:
A kind of synthetic method of (1- cyclopropyl -1- methyl) ethylamine hydrochloride, the synthetic method are as follows:
The specific steps of the synthetic method are as follows:
Step 1, in anhydrous tetrahydrofuran solution, cyclopropanecarbonitrile reacts generation (1- cyclopropyl with lithium methide, cerous chloride
Base -1- methyl) ethylamine；
Step 2, aforementioned obtained (1- cyclopropyl -1- methyl) ethylamine crude product is dissolved in ethyl acetate, is then passed to
HCl gas reacts to obtain (1- cyclopropyl -1- methyl) ethylamine hydrochloride.
Preferably, the detailed process of the step 1 are as follows: cerous chloride is dissolved in anhydrous tetrahydro furan, in -70~-80
Lithium methide is added dropwise under the conditions of DEG C, the tetrahydrofuran solution of cyclopropanecarbonitrile is added dropwise after being added dropwise again, then warm naturally to 20~
30 DEG C the reaction was continued, and ammonium hydroxide quenching reaction, filtering reacting liquid is added to reaction solution after the reaction was completed, and filter cake is washed with methylene chloride
It washs, is concentrated to get (1- cyclopropyl -1- methyl) ethylamine crude product.
Preferably, the detailed process of the step 1 are as follows: cerous chloride is dissolved in anhydrous tetrahydro furan, in -70~-80
Lithium methide is added dropwise under the conditions of DEG C, is reacted 0.5~4 hour after being added dropwise, the tetrahydrofuran solution of cyclopropanecarbonitrile is then added dropwise again,
The reaction was continued 0.5~4 hour after being added dropwise, and then warming naturally to 20~30 DEG C, the reaction was continued 0.5~24 hour, has reacted
Ammonium hydroxide quenching reaction, filtering reacting liquid is added at backward reaction solution, filter cake is washed with methylene chloride, is concentrated to get (1- cyclopropyl-
1- methyl) ethylamine crude product.
Preferably, the molar ratio of the cerous chloride and cyclopropanecarbonitrile is 2:1~4:1；The lithium methide and cyclopropanecarbonitrile
Molar ratio be 3:1~5:1.
Preferably, the detailed process of the step 2 are as follows: (1- cyclopropyl -1- methyl) ethylamine crude product is dissolved in ethyl acetate
In, it is passed through HCl gas, until stopping reaction when solid is not further added by, filtering reacting liquid is dry after solid is washed with ethyl acetate
Obtain (1- cyclopropyl -1- methyl) ethylamine hydrochloride.
The present invention also provides a kind of synthetic method of (1- cyclopropyl -1- methyl) ethylamine, the synthetic methods are as follows:
Cerous chloride is dissolved in anhydrous tetrahydro furan, lithium methide is added dropwise under the conditions of -70~-80 DEG C, after being added dropwise
The tetrahydrofuran solution of cyclopropanecarbonitrile is added dropwise again, then warming naturally to 20~30 DEG C, the reaction was continued, after the reaction was completed to reaction
Ammonium hydroxide quenching reaction, filtering reacting liquid is added in liquid, and filter cake is washed with methylene chloride, is concentrated to get (1- cyclopropyl -1- methyl) second
Base amine crude product.
Preferably, the molar ratio of the cerous chloride and cyclopropanecarbonitrile is 2:1~4:1；The lithium methide and cyclopropanecarbonitrile
Molar ratio be 3:1~5:1.
Compared with prior art, beneficial effects of the present invention are as follows:
1, the present invention is using cyclopropanecarbonitrile as raw material, and directly and lithium methide, cerous chloride reaction obtain (N- chlorine sulphonyl
Base -1- cyclopropyl -1- methyl) ethylamine, further reacts with HCl gas and obtains (1- cyclopropyl -1- methyl) ethyl amine salt
Hydrochlorate.This method obtains target product, simple process and low cost, with higher yield and high-purity system by single step reaction
Obtain (1- cyclopropyl -1- methyl) ethylamine hydrochloride.
2, the invention avoids using Sodium azide and tetraethyl titanate to participate in reaction in the prior art, reaction condition is more warm
With, it is easily operated, and reaction process is stablized, and yield is higher, and cost greatly reduces, and is successfully exaggerated production.
Specific embodiment
Illustrate technical solution of the present invention below by way of specific embodiment.The equal city of raw materials and reagents used in the present invention
Selling can obtain.
Embodiment 1
Cerous chloride (238g, 0.9mol, 3.0eq) compound is dissolved in the anhydrous THF of 2L, is stirred at room temperature 2 hours, then
Reaction solution is cooled to -78 DEG C, and then (concentration of lithium methide is 1mol/L to the tetrahydrofuran solution of dropwise addition lithium methide, is added dropwise
1.2L), wherein the additional amount of lithium methide is (1.2mol, 4.0eq)；The reaction was continued after being added dropwise 1 hour, then reacts to this
The THF solution 60ml of cyclopropanecarbonitrile (20g, 0.30mol, 1.0eq) is added dropwise in liquid, after being added dropwise, the reaction was continued 1h, then instead
It answers liquid to be warmed to room temperature reaction 4h naturally, ammonium hydroxide 100ml quenching reaction, filtering reacting liquid, filter cake DCM is then added into reaction solution
Washing is concentrated filtrate, obtains crude product (1- cyclopropyl -1- methyl) ethylamine 20g,
Crude product (1- cyclopropyl -1- methyl) ethylamine 20g is dissolved into the ethyl acetate of 100ml, then Xiang Qitong
Enter HCl gas to the solid being precipitated not to be further added by, crosses filter solid, and be beaten 2 times with ethyl acetate, obtain pure compound (1-
Cyclopropyl -1- methyl) ethylamine hydrochloride (20.6g, 16.7mol), yield 50.8%.1H-NMR(300MHz,CD3OD):δ
1.22(s,6H),1.10-1.07(m,1H),0.61-0.49(m,4H)。
For embodiment 1, change the product yield of molar ratio, reaction temperature, reaction time acquisition of reactant referring to table
1。
Table 1 synthesizes the yield of (1- cyclopropyl -1- methyl) ethylamine hydrochloride
Embodiment 5
Cerous chloride (238g, 0.9mol, 3.0eq) compound is dissolved in the anhydrous THF of 2L, is stirred at room temperature 2 hours, then
Reaction solution is cooled to -78 DEG C, and then (concentration of lithium methide is 1mol/L to the tetrahydrofuran solution of dropwise addition lithium methide, is added dropwise
1.2L), wherein the additional amount of lithium methide is (1.2mol, 4.0eq)；The reaction was continued after being added dropwise 1 hour, then reacts to this
The THF solution 60ml of cyclopropanecarbonitrile (20g, 0.30mol, 1.0eq) is added dropwise in liquid, after being added dropwise, the reaction was continued 4h, then to
In reaction solution plus ammonium hydroxide 100ml quenching reaction, filtering reacting liquid, filter cake are washed with DCM, and filtrate is concentrated, obtains crude product (1- ring
Propyl -1- methyl) ethylamine 12g.
Crude product (1- cyclopropyl -1- methyl) ethylamine 12g is dissolved into the ethyl acetate of 100ml, then Xiang Qitong
Enter HCl gas to the solid being precipitated not to be further added by, crosses filter solid, and be beaten 2 times with ethyl acetate and obtain pure compound (1-
Cyclopropyl -1- methyl) ethylamine hydrochloride (9.6g, 0.07mol), yield 23.7%.
Embodiment 6
Cerous chloride (2380g, 9.6mol, 3.0eq) compound is dissolved in the anhydrous THF of 20L, is stirred at room temperature 2 hours, so
Reaction solution is cooled to -78 DEG C afterwards, and then (concentration of lithium methide is 1mol/L to the tetrahydrofuran solution of dropwise addition lithium methide, is added dropwise
12L), wherein the additional amount of lithium methide is (12mol, 4.0eq)；The reaction was continued 2.5 hours after being added dropwise, into this reaction solution
The THF solution 600ml of cyclopropanecarbonitrile (200g, 30mol, 1.0eq) is added dropwise, after being added dropwise, the reaction was continued 4h, then reaction solution
Naturally it is warmed to room temperature reaction overnight, ammonium hydroxide 1000ml quenching reaction is then added into reaction solution, stir 2 hours, filtering reacting liquid,
Filter cake is washed with DCM, and filtrate is concentrated, obtains crude product 195g.
Crude product 195g is dissolved into the ethyl acetate of 100ml, is then passed through HCl gas to the solid being precipitated to it
It is not further added by, crosses filter solid, and be beaten 2 times with ethyl acetate and obtain pure compound (1- cyclopropyl -1- methyl) ethyl amine salt
Hydrochlorate (192.6g, 1.42mol), yield 50.8%.
It above are only part preferred embodiment of the invention, the present invention is not limited in the content of embodiment.For ability
For technical staff in domain, can there are various change and change in the conception range of technical solution of the present invention, made
What changes and change, within that scope of the present invention.
Claims (6)
1. a kind of synthetic method of (1- cyclopropyl -1- methyl) ethylamine hydrochloride, the synthetic method are as follows:
The specific steps of the synthetic method are as follows:
Step 1, in anhydrous tetrahydrofuran solution, cyclopropanecarbonitrile reacts generation (1- cyclopropyl -1- with lithium methide, cerous chloride
Methyl) ethylamine；
Step 2, aforementioned obtained (1- cyclopropyl -1- methyl) ethylamine crude product is dissolved in ethyl acetate, then passes to hydrochloric acid
Gas reaction obtains (1- cyclopropyl -1- methyl) ethylamine hydrochloride；
The detailed process of the step 1 are as follows: cerous chloride is dissolved in anhydrous tetrahydro furan, is added dropwise under the conditions of -70~-80 DEG C
Lithium methide, is added dropwise the tetrahydrofuran solution of cyclopropanecarbonitrile again after being added dropwise, then warming naturally to 20~30 DEG C, the reaction was continued,
Ammonium hydroxide quenching reaction, filtering reacting liquid is added to reaction solution after the reaction was completed, filter cake is washed with methylene chloride, is concentrated to get (1-
Cyclopropyl -1- methyl) ethylamine crude product.
2. the synthetic method of one kind (1- cyclopropyl -1- methyl) ethylamine hydrochloride as described in claim 1, feature exist
In the detailed process of the step 1 are as follows: cerous chloride is dissolved in anhydrous tetrahydro furan, is added dropwise under the conditions of -70~-80 DEG C
Lithium methide reacts 0.5~4 hour after being added dropwise, the tetrahydrofuran solution of cyclopropanecarbonitrile is then added dropwise again, is added dropwise subsequent
Continuous reaction 0.5~4 hour, then warming naturally to 20~30 DEG C, the reaction was continued 0.5~24 hour, after the reaction was completed to reaction solution
Ammonium hydroxide quenching reaction, filtering reacting liquid is added, filter cake is washed with methylene chloride, is concentrated to get (1- cyclopropyl -1- methyl) ethyl
Amine crude product.
3. such as a kind of described in any item synthetic methods of (1- cyclopropyl -1- methyl) ethylamine hydrochloride of claim 1-2,
Be characterized in that: the molar ratio of the cerous chloride and cyclopropanecarbonitrile is 2:1~4:1；Mole of the lithium methide and cyclopropanecarbonitrile
Than for 3:1~5:1.
4. the synthetic method of one kind (1- cyclopropyl -1- methyl) ethylamine hydrochloride as described in claim 1, feature exist
In the detailed process of the step 2 are as follows: (1- cyclopropyl -1- methyl) ethylamine crude product is dissolved in ethyl acetate, is passed through hydrogen chloride gas
Body, until stopping reaction when solid is not further added by, filtering reacting liquid after solid is washed with ethyl acetate, is dried to obtain (1- cyclopropyl
Base -1- methyl) ethylamine hydrochloride.
5. a kind of synthetic method of (1- cyclopropyl -1- methyl) ethylamine, the synthetic method are as follows:
Cerous chloride is dissolved in anhydrous tetrahydro furan, lithium methide is added dropwise under the conditions of -70~-80 DEG C, is dripped again after being added dropwise
Add the tetrahydrofuran solution of cyclopropanecarbonitrile, then warming naturally to 20~30 DEG C, the reaction was continued, adds after the reaction was completed to reaction solution
Enter ammonium hydroxide quenching reaction, filtering reacting liquid, filter cake is washed with methylene chloride, is concentrated to get (1- cyclopropyl -1- methyl) ethylamine
Crude product.
6. the synthetic method of one kind (1- cyclopropyl -1- methyl) ethylamine hydrochloride as claimed in claim 5, feature exist
In: the molar ratio of the cerous chloride and cyclopropanecarbonitrile is 2:1~4:1；The molar ratio of the lithium methide and cyclopropanecarbonitrile is 3:1
~5:1.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010141538A1 (en) * | 2009-06-03 | 2010-12-09 | Glaxosmithkline Llc | Bis-pyridylpyridones as melanin-concentrating hormone receptor 1 antagonists |
| CN103664697A (en) * | 2012-09-07 | 2014-03-26 | 博瑞生物医药技术(苏州)有限公司 | Chemical method used for preparing aromatic cyclopropanecarbonitrile and cyclopropylamine |
-
2016
- 2016-12-30 CN CN201611265611.4A patent/CN106631824B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010141538A1 (en) * | 2009-06-03 | 2010-12-09 | Glaxosmithkline Llc | Bis-pyridylpyridones as melanin-concentrating hormone receptor 1 antagonists |
| CN103664697A (en) * | 2012-09-07 | 2014-03-26 | 博瑞生物医药技术(苏州)有限公司 | Chemical method used for preparing aromatic cyclopropanecarbonitrile and cyclopropylamine |
Non-Patent Citations (1)
| Title |
|---|
| "Synthetic Routes to Cyclopropyl- Substituted Azoalkanes. Some Reactions of Cpclopropylcarbinyl Cyanates, Isocyanates, Benzoates, and p-Nitrobenzoates";JACK W.TIMBERLAKE, et al.;《The Journal of Organic Chemistry》;19681130;第33卷(第11期);4054-4060 |
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