CN111153807B - Preparation method of N, N-dimethylamino chloropropane hydrochloride - Google Patents
Preparation method of N, N-dimethylamino chloropropane hydrochloride Download PDFInfo
- Publication number
- CN111153807B CN111153807B CN202010046724.5A CN202010046724A CN111153807B CN 111153807 B CN111153807 B CN 111153807B CN 202010046724 A CN202010046724 A CN 202010046724A CN 111153807 B CN111153807 B CN 111153807B
- Authority
- CN
- China
- Prior art keywords
- chloropropene
- preparation
- reaction
- catalyst
- chloropropane hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- FCMCDVRJVMDKAQ-UHFFFAOYSA-N 1-chloro-n,n-dimethylpropan-1-amine;hydrochloride Chemical compound Cl.CCC(Cl)N(C)C FCMCDVRJVMDKAQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims description 23
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MSUCLKFPHDRRGG-UHFFFAOYSA-N 1-chloro-n,n-dimethylpropan-1-amine Chemical compound CCC(Cl)N(C)C MSUCLKFPHDRRGG-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000005966 aza-Michael addition reaction Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 229960005426 doxepin Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 201000003102 mental depression Diseases 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and particularly relates to a preparation method of N, N-dimethylamino chloropropane hydrochloride. The preparation method has the advantages of high reaction speed, high conversion rate, good selectivity, simple post-treatment and the like, and the product purity is over 99.0 percent and the molar yield is over 88 percent.
Description
Technical Field
The invention belongs to the technical field of synthesis of drug intermediates, and particularly relates to a preparation method of N, N-dimethylamino chloropropane hydrochloride.
Background
The N, N-dimethylamino hydrochloride is used for synthesizing chlorpromazine which is a psychotropic drug and imipramine which is an antidepressant, and is also a key intermediate of Telden, doxepin, amitriptyline and the like. The medicaments have the functions of resisting mental disorder, depression and anxiety, and also have obvious curative effects on the aspects of diminishing inflammation, relieving fever, easing pain and the like, and the structural formula of the medicaments is as follows:
according to the prior literature reports, the following main synthetic routes are available:
the first synthetic route is as follows:
the reaction conditions of the method are harsh, a large amount of SO2 gas can be generated by using thionyl chloride in the chlorination process of the hydroxyl in the second step, a special absorption tower is needed for tail gas absorption, the equipment investment is large, the three wastes are high, and the method is not environment-friendly.
The second synthetic route is as follows:
according to the method, chloropropene is used as a raw material, the chloropropene and dimethylamine gas are subjected to high-temperature pressurization reaction under the action of strong alkali through gasification, and then hydrogen chloride gas is introduced to perform addition and salt formation, so that the reaction steps are complex, a large number of byproducts are produced, and the yield is low.
The third synthetic route is as follows:
the method takes 1,3-bromochloropropane and dimethylamine as reaction raw materials, and performs amine alkylation substitution reaction under the action of a catalyst, but by-products N, N, N ', N' tetramethyl-1,3-propane diamine are generated in the reaction process of the process, which brings trouble to the purification of products in the post-treatment process, directly influences the yield and quality of the products, and simultaneously generates a large amount of by-products hydrogen bromide or hydrogen chloride gas, so that the method has many three wastes and is not beneficial to energy conservation and environmental protection.
Disclosure of Invention
Based on the related technical problems, the invention aims to provide a preparation method of N, N-dimethylamino chloropropane hydrochloride, which aims to solve the problems that the existing preparation method of N, N-dimethylamino chloropropane hydrochloride is relatively complex and has more byproducts.
In order to achieve the purpose, the invention adopts the following technical scheme:
the preparation method of the N, N-dimethylamino chloropropane hydrochloride comprises the following synthetic route:
the method specifically comprises the following steps:
1) Reacting the chloropropene solution with dimethylamine for 1-10h at 35-45 ℃ under the action of a catalyst (the content of chloropropene in the raw material is less than or equal to 2 percent through gas phase tracking detection), and then terminating the reaction;
2) Carrying out reduced pressure distillation on the reaction product obtained in the step 1), washing and layering, adding acid into the obtained organic layer until the pH value is 2-3, reacting for 1-2 h at the temperature of 95-112 ℃, refluxing and carrying water for 8-10h, cooling to normal temperature, filtering, and drying to obtain the N, N-dimethylamino chloropropane hydrochloride.
Specifically, the chloropropene solution in the step 1) is obtained by dissolving chloropropene in toluene, ethanol or water, and the chloropropene solution is preferably obtained by dissolving chloropropene in toluene or ethanol.
In particular, the catalyst in step 1) may be a metal catalyst such as TiCl 4 Or SnCl 4 Can be a supported catalyst such as CeCl 3 ·7H 2 O or NaI, or a recoverable catalyst formed by mixing with silica gel, such as diatomaceous earth.
Specifically, the molar ratio of dimethylamine to chloropropene in the step 1) is (1.1-1.5): 1.
specifically, the mass of the catalyst added in the step 1) is 0.2-1.0% of that of chloropropene.
Compared with the prior art, the invention has the beneficial effects that:
the invention takes dimethylamine as raw material, carries out aza Michael addition with chloropropene under the action of catalyst, obtains N, N-dimethylamino chloropropane by separation and purification after the reaction is finished, obtains N, N-dimethylamino chloropropane hydrochloride by acidification and salt forming reaction, has no by-product, has the advantages of simple reaction process, simple and convenient post-treatment process, high conversion rate of main raw material, high reaction speed and the like, and the obtained product has high purity (more than 99.0 percent).
Detailed Description
In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The molar yield calculation method of the invention comprises the following steps: taking chloropropene as a reference, the material input is 50.0g, the molar weight is 0.65mol, the theoretical product yield is 103.3g, and the actual yield is divided by the theoretical yield to obtain the molar yield.
Example 1
A preparation method of N, N-dimethylamino chloropropane hydrochloride comprises the following specific steps:
1) Adding 50.0g of chloropropene and 150g of toluene into a four-mouth reaction bottle, stirring, and adding a catalyst TiCl 4 0.5g, 33g of dimethylamine gas introduced at 35 ℃, reaction is stopped after heat preservation at 35 ℃ for 7h, and the chloropropene content is less than or equal to 2% by gas phase tracking detection analysis;
2) Distilling the reaction product in the step 1) under reduced pressure, recovering 45.2g of toluene and unreacted vinyl chloride, washing with 100g of water for layering, and removing the catalyst TiCl 4 (catalyst TiCl) 4 Dissolved in a water layer), hydrochloric acid is dripped into the organic layer, the pH value is adjusted to 2-3, the reaction and the reflux carry water for 10 hours at the temperature of 95 ℃, the temperature is reduced to normal temperature, the filtration and the drying are carried out, and 92.1g of N, N-dimethylamino chloropropane hydrochloride with the purity of 99.2 percent and the molar yield of 89.2 percent are obtained.
Example 2
A preparation method of N, N-dimethylamino chloropropane hydrochloride comprises the following specific steps:
1) Adding 50.0g of chloropropene and 150g of ethanol into a four-mouth reaction bottle, stirring, and adding a catalyst TiCl 4 Introducing 36g of dimethylamine gas at the temperature of 40 ℃ in 1.0g, keeping the temperature at the temperature of 40 ℃ for reaction for 8 hours, and then terminating the reaction, wherein the chloropropene content is less than or equal to 2% by gas phase tracking detection analysis;
2) Distilling the reaction product in the step 1) under reduced pressure, recovering 36.4g of toluene and unreacted vinyl chloride, washing with 100g of water for layering, and removing the catalyst TiCl 4 (catalyst TiCl) 4 Dissolved in a water layer), hydrogen chloride gas is introduced into the organic layer, the pH value is adjusted to 2-3, the reaction and the reflux are carried out for 10 hours at the temperature of 100 ℃, the temperature is reduced to normal temperature, the filtration and the drying are carried out, and 91.5g of N, N-dimethylamino chloropropane hydrochloride with the purity of 99.4 percent and the molar yield of 88.6 percent are obtained.
Example 3
A preparation method of N, N-dimethylamino chloropropane hydrochloride comprises the following specific steps:
1) Adding 50.0g of chloropropene and 150g of toluene into a four-opening reaction bottle, stirring, adding 1.0g of catalyst diatomite, introducing 38g of dimethylamine gas at 45 ℃, keeping the temperature at 45 ℃ for reaction for 10 hours, and then terminating the reaction, wherein the content of chloropropene is less than or equal to 2% by gas phase tracking detection analysis;
2) And (2) carrying out reduced pressure distillation on the reaction product in the step 1), recovering 42.1g of toluene and unreacted vinyl chloride, washing with 100g of water, filtering to remove catalyst diatomite, dropwise adding hydrochloric acid into the organic layer, adjusting the pH value to 2-3, carrying out reaction and reflux at 112 ℃ for 12h with water, cooling to normal temperature, filtering, and drying to obtain 93.0g of N, N-dimethylamino chloropropane hydrochloride, wherein the purity is 99.1%, and the molar yield is 90.0%.
While particular embodiments of the present invention have been described, it is to be understood that the present invention is not limited to the precise embodiments described above, and that various changes and modifications may be effected therein by one skilled in the art without departing from the scope or spirit of the invention as defined in the appended claims.
Claims (3)
1. The preparation method of the N, N-dimethylamino chloropropane hydrochloride is characterized by comprising the following steps:
1) Reacting chloropropene solution with dimethylamine for 1-10h at 35-45 ℃ under the action of a catalyst, and terminating the reaction;
2) Carrying out reduced pressure distillation on the reaction product obtained in the step 1), washing and layering, adding acid into the obtained organic layer until the pH value is 2-3, reacting for 1-2 h at the temperature of 95-112 ℃, refluxing for 8-10h with water, cooling to normal temperature, filtering, and drying to obtain N, N-dimethylamino chloropropane hydrochloride;
the catalyst in the step 1) is TiCl 4 Or diatomaceous earth;
the chloropropene solution in the step 1) is obtained by dissolving chloropropene in toluene or ethanol.
2. The preparation method according to claim 1, wherein the molar ratio of dimethylamine to chloropropene in step 1) is (1.1-1.5): 1.
3. the process according to claim 1, wherein the amount of the catalyst added in step 1) is 0.2 to 1.0% by mass or 2.0% by mass based on the amount of the chloropropene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010046724.5A CN111153807B (en) | 2020-01-16 | 2020-01-16 | Preparation method of N, N-dimethylamino chloropropane hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010046724.5A CN111153807B (en) | 2020-01-16 | 2020-01-16 | Preparation method of N, N-dimethylamino chloropropane hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111153807A CN111153807A (en) | 2020-05-15 |
| CN111153807B true CN111153807B (en) | 2023-01-06 |
Family
ID=70563483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010046724.5A Active CN111153807B (en) | 2020-01-16 | 2020-01-16 | Preparation method of N, N-dimethylamino chloropropane hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111153807B (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060468C (en) * | 1998-06-01 | 2001-01-10 | 贵州群星科学技术经济合作公司 | Refining method of dimethyl allylamine and its salt |
| SK5202000A3 (en) * | 2000-04-07 | 2001-12-03 | Slovakofarma As | Method for the preparation of (e)-n-(6,6-dimethyl-2-hepten-4- inyl)-n-methyl-1-naphthalenemethylamine (terbinaphin) |
| CN103121976A (en) * | 2012-12-07 | 2013-05-29 | 苏州百灵威超精细材料有限公司 | Preparation method of N-monosubstituted homopiperazines |
| CN107188810A (en) * | 2017-07-17 | 2017-09-22 | 启东市瑞丰化工有限公司 | A kind of chloropropane hydrochloride of N, N dimethylamino 3 and preparation technology |
| CN108516941B (en) * | 2018-03-26 | 2021-05-18 | 济南大学 | A kind of preparation method of 3-(phenylamino) ethyl propionate compound |
-
2020
- 2020-01-16 CN CN202010046724.5A patent/CN111153807B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN111153807A (en) | 2020-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102924424B (en) | Method for synthesizing doxepin hydrochloride | |
| CN104557567B (en) | A kind of preparation method of memantine | |
| CN103012275A (en) | Method for producing high-purity N-alkyl imidazole | |
| CN111153807B (en) | Preparation method of N, N-dimethylamino chloropropane hydrochloride | |
| CN106631823B (en) | Preparation method of lorcaserin intermediate | |
| CN104370746B (en) | A kind of cost-effective preparation method to nitrobenzyl alcohol | |
| CN103360264A (en) | Synthesizing method of indacaterol amino fragment 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride | |
| CN110590706B (en) | Preparation method of N-methylpyrrolidine | |
| CN113264814A (en) | Process for preparing hydroxytyrosol | |
| CN107056685A (en) | A kind of synthetic method of doxylamine succinate | |
| CN108047032B (en) | Method for the synthesis of glutaric acid from alpha-ketoglutaric acid | |
| CN110627754A (en) | A kind of method utilizing continuous flow microchannel reactor to prepare 2-oxo-2-furyl acetic acid | |
| CN101412678B (en) | Method for synthesizing memantine hydrochloride | |
| CN112552184B (en) | Synthetic method of cyclopropyl-containing chiral amine hydrochloride | |
| CN113943231A (en) | Preparation method of 1-hydroxymethyl cyclopropyl acetonitrile | |
| CN111574420B (en) | Preparation method of aminopyrrolidine | |
| CN114149335A (en) | Synthesis method of 4, 4' -diaminodiphenyl ether by taking parachloroaniline as initial raw material | |
| CN103420939B (en) | Method for synthesizing azacycloheptane | |
| CN109180441B (en) | Synthetic method of triethyl orthoformate | |
| CN107162920A (en) | A kind of preparation method of R-1- amino -2- propyl alcohol | |
| CN112851632A (en) | Method for efficiently preparing thiophene medical intermediate | |
| CN115850039B (en) | Method for synthesizing cyclopropylmethyl ketone through imine intermediate | |
| CN114853619B (en) | Preparation method of N-methyltyramine hydrochloride suitable for industrial production | |
| CN112142579A (en) | Preparation process of 2-hydroxy-4-methoxybenzophenone | |
| CN110922341A (en) | Preparation method of methoxylamine hydrochloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |