CN106699576A - Method for synthesizing methoxyphenamine hydrochloride - Google Patents
Method for synthesizing methoxyphenamine hydrochloride Download PDFInfo
- Publication number
- CN106699576A CN106699576A CN201611206130.6A CN201611206130A CN106699576A CN 106699576 A CN106699576 A CN 106699576A CN 201611206130 A CN201611206130 A CN 201611206130A CN 106699576 A CN106699576 A CN 106699576A
- Authority
- CN
- China
- Prior art keywords
- reaction
- methoxyphenamine
- schiff bases
- added
- alkali
- 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.)
- Pending
Links
- 229960000659 methoxyphenamine hydrochloride Drugs 0.000 title claims abstract description 17
- FGSJNNQVSUVTPW-UHFFFAOYSA-N methoxyphenamine hydrochloride Chemical compound Cl.CNC(C)CC1=CC=CC=C1OC FGSJNNQVSUVTPW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title abstract description 6
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- 239000002262 Schiff base Substances 0.000 claims abstract description 41
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 41
- GMBFNZCPZFVKAT-UHFFFAOYSA-N 1-(2-methoxyphenyl)propan-2-one Chemical compound COC1=CC=CC=C1CC(C)=O GMBFNZCPZFVKAT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims description 29
- 229960005405 methoxyphenamine Drugs 0.000 claims description 27
- 239000003513 alkali Substances 0.000 claims description 23
- OEHAYUOVELTAPG-UHFFFAOYSA-N methoxyphenamine Chemical compound CNC(C)CC1=CC=CC=C1OC OEHAYUOVELTAPG-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 claims description 13
- 238000010189 synthetic method Methods 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012448 Lithium borohydride Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- UESSEMPSSAXQJC-UHFFFAOYSA-N ethanol;methanamine Chemical compound NC.CCO UESSEMPSSAXQJC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- -1 methoxyphenamine hydrochlorides Chemical class 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000006197 hydroboration reaction Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 description 1
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940036543 ionamin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of synthesis of medicinal raw materials and chemical intermediates, in particular to a method for synthesizing methoxyphenamine hydrochloride. The method comprises the following steps: adding o-methoxyl phenylacetone and a methylamine ethanol solution into a reaction kettle, performing a reaction to obtain Schiff base, and further adding a metal reducing agent into the Schiff base obtained through the reaction to reduce the Schiff base. The method for synthesizing the methoxyphenamine hydrochloride is low in cost, high in product content and easy to industrialize, and the mole yield is greater than 82%.
Description
Technical field
The present invention relates to the technical field that medical material and chemical intermediate synthesize, especially a kind of methoxyphenamine hydrochloride
Synthetic method.
Background technology
Methoxyphenamine hydrochloride, chemical name：2- methoxyl group-N, the hydrochloride of Ionamin is that beta-2 adrenoceptor swashs
Dynamic medicine, the effect of bronchial spasm is released with lax bronchial smooth muscle.Its antiasthmatic effect is better than ephedrine, central excitation and
Cardiovascular aspect is then weaker.At present, the synthetic method of methoxyphenamine hydrochloride is reacted using metal catalyzed hydrogenation mostly：
Zenichi H etc. report another synthetic method (Yakugaku Zasshi, 1957,77：256-8.), adjacent first
The methylamine methanol solution of phenyl acetone 3g and 20g 30%, 1.6g is obtained under the catalytic hydrogenation of Raney's nickel and platinous chloride
Product.
Chinese Patent Application No. is that 200910264415.9 patent application discloses a kind of synthesis of methoxyphenamine hydrochloride
Method, in the catalytic hydrogenation of o-methoxyphenyl acetone and methylamine alcohol solution, it is catalyst to use palladium carbon.
In above-mentioned use o-methoxyphenyl acetone and the method for methylamine methyl alcohol reaction, platinum oxide, platinous chloride, palladium carbon are used
Make catalyst, catalyst is expensive, production cost can be dramatically increased；And molar yield is not high.
The content of the invention
The technical problem to be solved in the present invention is：To overcome the deficiencies in the prior art, there is provided a kind of low cost, product
Product content is high, the synthetic method of the methoxyphenamine hydrochloride of easy industrialization, molar yield more than 82%.
The technical solution adopted for the present invention to solve the technical problems is：
Reaction formula is as follows：
The synthetic method of methoxyphenamine hydrochloride, enters during o-methoxyphenyl acetone and methylamine methanol solution are added into reactor
Row reaction, reaction obtains schiff bases；Adding metallic reducing agent in the schiff bases that reaction is obtained again carries out the reduction of schiff bases.
Specific synthesis step is as follows：
Step 1：Synthesis schiff bases：Carried out instead during o-methoxyphenyl acetone and methylamine methanol solution are added into reactor
Should, the reaction time is 15~18h, and reaction temperature is 20~35 DEG C, fully obtains schiff bases after reaction；
Step 2：Synthesis methoxyphenamine alkali：Metallic reducing agent is added in the schiff bases that step 1 reaction is obtained carries out Schiff
The reduction of alkali, the reaction time is 6~12h, and reaction temperature is -5~5 DEG C, fully obtains methoxyphenamine alkali after reaction；
Step 3：Synthetic hydrochloric acid methoxyphenamine：In the methoxyphenamine alkali that step 2 reaction is obtained, hydrochloric acid solution regulation is added
PH=1~2, the reaction time is 11~12h, and reaction temperature is -10~-5 DEG C, fully obtains methoxyphenamine hydrochloride after reaction.
The metallic reducing agent is in Lithium Aluminium Hydride, sodium cyanoborohydride, lithium borohydride or sodium triacetoxy borohydride
One kind.
The quality consumption of the metallic reducing agent is 0.18~0.2 times of o-methoxyphenyl acetone quality.
The beneficial effects of the invention are as follows：Using Lithium Aluminium Hydride, sodium cyanoborohydride, lithium borohydride or triacetoxy borohydride hydrogen
Change a kind of reduction for carrying out schiff bases in sodium, substantially reduce reaction cost, molar yield is more than 82%, is capable of achieving industrialization.
Specific embodiment
The present invention is further detailed explanation now.
Reaction formula is as follows：
Embodiment 1：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 15h, and reaction temperature is 28 DEG C, fully obtains schiff bases after reaction, adds 17g Lithium Aluminium Hydrides to enter in schiff bases
The reduction of row schiff bases, the reaction time is 7h, and reaction temperature is 2 DEG C, fully methoxyphenamine alkali is obtained after reaction, in methoxyphenamine
Hydrochloric acid solution regulation PH=2 is added in alkali, the reaction time is 12h, and reaction temperature is -6 DEG C, fully obtains 118.5g salt after reaction
Sour methoxyphenamine, molar yield is 90.2%.
Embodiment 2：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 16h, and reaction temperature is 25 DEG C, fully obtains schiff bases after reaction, and 18g cyano group hydroborations are added in schiff bases
Sodium carries out the reduction of schiff bases, and the reaction time is 6h, and reaction temperature is 3 DEG C, fully methoxyphenamine alkali is obtained after reaction, in methoxy
Hydrochloric acid solution regulation PH=1 is added in that bright alkali, the reaction time is 11h, and reaction temperature is -5 DEG C, is fully obtained after reaction
116.4g methoxyphenamine hydrochlorides, molar yield is 88.6%.
Embodiment 3：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 15h, and reaction temperature is 28 DEG C, fully obtains schiff bases after reaction, adds 17g lithium borohydrides to enter in schiff bases
The reduction of row schiff bases, the reaction time is 10h, and reaction temperature is 0 DEG C, fully obtains methoxyphenamine alkali after reaction, methoxy that
Hydrochloric acid solution regulation PH=2 is added in bright alkali, the reaction time is 12h, and reaction temperature is -8 DEG C, fully obtains 112.6g after reaction
Methoxyphenamine hydrochloride, molar yield is 85.7%.
Embodiment 4：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 17h, and reaction temperature is 20 DEG C, fully obtains schiff bases after reaction, and 19g triacetoxyl groups are added in schiff bases
Sodium borohydride carries out the reduction of schiff bases, and the reaction time is 9h, and reaction temperature is 1 DEG C, fully obtains methoxyphenamine alkali after reaction,
Hydrochloric acid solution regulation PH=1 is added in methoxyphenamine alkali, the reaction time is 11h, and reaction temperature is -7 DEG C, fully after reaction
To 111.5g methoxyphenamine hydrochlorides, molar yield is 84.9%.
Embodiment 5：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 16h, and reaction temperature is 30 DEG C, fully obtains schiff bases after reaction, adds 18g Lithium Aluminium Hydrides to enter in schiff bases
The reduction of row schiff bases, the reaction time is 8h, and reaction temperature is 0 DEG C, fully methoxyphenamine alkali is obtained after reaction, in methoxyphenamine
Hydrochloric acid solution regulation PH=2 is added in alkali, the reaction time is 12h, and reaction temperature is -8 DEG C, fully obtains 116.8g salt after reaction
Sour methoxyphenamine, molar yield is 88.9%.
Embodiment 6：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 17h, and reaction temperature is 27 DEG C, fully obtains schiff bases after reaction, and 19g cyano group hydroborations are added in schiff bases
Sodium carries out the reduction of schiff bases, and the reaction time is 7h, and reaction temperature is 1 DEG C, fully methoxyphenamine alkali is obtained after reaction, in methoxy
Hydrochloric acid solution regulation PH=1 is added in that bright alkali, the reaction time is 11h, and reaction temperature is -7 DEG C, is fully obtained after reaction
113.9g methoxyphenamine hydrochlorides, molar yield is 86.7%.
Embodiment 7：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 16h, and reaction temperature is 30 DEG C, fully obtains schiff bases after reaction, adds 18g lithium borohydrides to enter in schiff bases
The reduction of row schiff bases, the reaction time is 12h, and reaction temperature is -2 DEG C, fully obtains methoxyphenamine alkali after reaction, methoxy that
Hydrochloric acid solution regulation PH=2 is added in bright alkali, the reaction time is 12h, and reaction temperature is -10 DEG C, is fully obtained after reaction
109.7g methoxyphenamine hydrochlorides, molar yield is 83.5%.
Embodiment 8：Reacted during 100g o-methoxyphenyls acetone and 330g methylamine methanol solutions are added into reactor,
Reaction time is 18h, and reaction temperature is 24 DEG C, fully obtains schiff bases after reaction, and 20g triacetoxyl groups are added in schiff bases
Sodium borohydride carries out the reduction of schiff bases, and the reaction time is 11h, and reaction temperature is -1 DEG C, fully obtains methoxyphenamine after reaction
Alkali, adds hydrochloric acid solution regulation PH=1 in methoxyphenamine alkali, and the reaction time is 11h, and reaction temperature is -9 DEG C, fully reaction
After obtain 108.1g methoxyphenamine hydrochlorides, molar yield is 82.3%.
Molar yield in each embodiment, as shown in table 1：
With above-mentioned according to desirable embodiment of the invention as enlightenment, relevant staff completely can be without departing from this hair
In the range of bright technological thought, various changes and amendments are carried out.The technical scope of this invention is not limited to explanation
Content on book, it is necessary to its technical scope is determined according to right.
Claims (4)
1. the synthetic method of methoxyphenamine hydrochloride, it is characterized in that：O-methoxyphenyl acetone and methylamine methanol solution are added anti-
Answer and reacted in kettle, reaction obtains schiff bases；Adding metallic reducing agent in the schiff bases that reaction is obtained again carries out schiff bases
Reduction.
2. the synthetic method of methoxyphenamine hydrochloride as claimed in claim 1, it is characterized in that：Specific synthesis step is as follows：
Step 1：Synthesis schiff bases：Reacted during o-methoxyphenyl acetone and methylamine methanol solution are added into reactor, instead
It is 15~18h between seasonable, reaction temperature is 20~35 DEG C, fully obtains schiff bases after reaction；
Step 2：Synthesis methoxyphenamine alkali：Metallic reducing agent is added in the schiff bases that step 1 reaction is obtained carries out schiff bases
Reduction, the reaction time is 6~12h, and reaction temperature is -5~5 DEG C, fully obtains methoxyphenamine alkali after reaction；
Step 3：Synthetic hydrochloric acid methoxyphenamine：In the methoxyphenamine alkali that step 2 reaction is obtained, hydrochloric acid solution regulation PH=is added
1~2, the reaction time is 11~12h, and reaction temperature is -10~-5 DEG C, fully obtains methoxyphenamine hydrochloride after reaction.
3. the synthetic method of methoxyphenamine hydrochloride as claimed in claim 1, it is characterized in that：The metallic reducing agent is tetrahydrochysene aluminium
One kind in lithium, sodium cyanoborohydride, lithium borohydride or sodium triacetoxy borohydride.
4. the synthetic method of methoxyphenamine hydrochloride as claimed in claim 1, it is characterized in that：The quality consumption of the metallic reducing agent
It is 0.18~0.2 times of o-methoxyphenyl acetone quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611206130.6A CN106699576A (en) | 2016-12-23 | 2016-12-23 | Method for synthesizing methoxyphenamine hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611206130.6A CN106699576A (en) | 2016-12-23 | 2016-12-23 | Method for synthesizing methoxyphenamine hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106699576A true CN106699576A (en) | 2017-05-24 |
Family
ID=58903136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611206130.6A Pending CN106699576A (en) | 2016-12-23 | 2016-12-23 | Method for synthesizing methoxyphenamine hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106699576A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754549A (en) * | 2021-09-07 | 2021-12-07 | 青海制药厂有限公司 | Preparation method of aralkylamine compound and salt thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6331636B1 (en) * | 1989-05-31 | 2001-12-18 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| CN102267917A (en) * | 2011-06-15 | 2011-12-07 | 浙江工业大学 | Method for synthesizing methoxyphenamine hydrochloride |
| US20130331429A1 (en) * | 2009-12-22 | 2013-12-12 | Peter Gmeiner | Aminotetraline derivatives |
| WO2013183656A1 (en) * | 2012-06-04 | 2013-12-12 | 大日本住友製薬株式会社 | Conjugate of g-protein coupled receptor binding ligand and nucleic acid molecule |
| CN104926749A (en) * | 2015-06-25 | 2015-09-23 | 华中科技大学 | Benzoxazine monomer comprising vinyl benzene structure, and application and preparation method of benzoxazine monomer |
| CN105315221A (en) * | 2014-08-04 | 2016-02-10 | 中国科学院化学研究所 | Aromatic diamine type benzoxazine resin and preparation method thereof |
| CN105669469A (en) * | 2016-03-03 | 2016-06-15 | 常州瑞明药业有限公司 | Synthesis method of methoxyphenamine hydrochloride |
| CN106083689A (en) * | 2016-06-14 | 2016-11-09 | 齐鲁制药有限公司 | A kind of new preparation process of Silodosin compound |
-
2016
- 2016-12-23 CN CN201611206130.6A patent/CN106699576A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6331636B1 (en) * | 1989-05-31 | 2001-12-18 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| US20130331429A1 (en) * | 2009-12-22 | 2013-12-12 | Peter Gmeiner | Aminotetraline derivatives |
| CN102267917A (en) * | 2011-06-15 | 2011-12-07 | 浙江工业大学 | Method for synthesizing methoxyphenamine hydrochloride |
| WO2013183656A1 (en) * | 2012-06-04 | 2013-12-12 | 大日本住友製薬株式会社 | Conjugate of g-protein coupled receptor binding ligand and nucleic acid molecule |
| CN105315221A (en) * | 2014-08-04 | 2016-02-10 | 中国科学院化学研究所 | Aromatic diamine type benzoxazine resin and preparation method thereof |
| CN104926749A (en) * | 2015-06-25 | 2015-09-23 | 华中科技大学 | Benzoxazine monomer comprising vinyl benzene structure, and application and preparation method of benzoxazine monomer |
| CN105669469A (en) * | 2016-03-03 | 2016-06-15 | 常州瑞明药业有限公司 | Synthesis method of methoxyphenamine hydrochloride |
| CN106083689A (en) * | 2016-06-14 | 2016-11-09 | 齐鲁制药有限公司 | A kind of new preparation process of Silodosin compound |
Non-Patent Citations (6)
| Title |
|---|
| KUCKLAENDER, UWE等: "Synthesis and oxidation of 2-(2,5-dihydroxyphenyl)ethylamine derivatives. II", 《ZEITSCHRIFT FUER NATURFORSCHUNG, B: CHEMICAL SCIENCES》 * |
| MARTINE LARGERON等: "Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and Its 6-(N-Acetylcystein-S-yl) Conjugate", 《CHEM. RES. TOXICOL.》 * |
| NOGGLE, F. TAYLOR, JR.等: "Liquid chromatographic and mass spectral analysis of methoxyamphetamines and methoxymethamphetamines", 《JOURNAL OF CHROMATOGRAPHIC SCIENCE》 * |
| RF BORCH ， MD BERNSTEIN ， HD DURST: "Cyanohydridoborate anion as a selective reducing agent", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| YOUJUN ZHOU等: "Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives", 《J. MED. CHEM.》 * |
| 钟为慧等: "盐酸甲氧那明的合成工艺研究", 《化工生产与技术》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754549A (en) * | 2021-09-07 | 2021-12-07 | 青海制药厂有限公司 | Preparation method of aralkylamine compound and salt thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113173900A (en) | Synthetic method of vitreous chromogen | |
| CN104263796A (en) | Preparation method of R-1-aminotetralin | |
| CN104263797A (en) | Preparation method of R-1-aminotetralin | |
| CN108863822B (en) | Method for refining isoproterenol hydrochloride | |
| CN106699576A (en) | Method for synthesizing methoxyphenamine hydrochloride | |
| CN101979376B (en) | Method for preparing glycinamide hydrochloride | |
| CN104788326A (en) | Synthesis method of ambroxol hydrochloride | |
| CN103232356B (en) | Technology for preparing 3-phenyl-4-aminobutyric acid hydrochloride | |
| CN111454240B (en) | Process for preparing diselenide compounds | |
| CN104072391A (en) | Synthesis process of rivastigmine hydrogen tartrate | |
| CN110317194A (en) | A kind of molecular sieve catalytic synthesis uncommon method for Buddhist nun difficult to understand | |
| CN101712623B (en) | Method for synthesizing methoxyphenamine hydrochloride | |
| CN111072505A (en) | Preparation method of venlafaxine impurity | |
| CN114685349B (en) | Process for preparing cis-exo-bicyclo [2.2.1] heptane-2, 3-dicarboximide | |
| CN105646617A (en) | Method for preparing tulathromycin | |
| CN113912507A (en) | A kind of preparation method of salbutamol impurity | |
| CN101481335A (en) | Rivastigmine intermediate preparation | |
| CN102775313A (en) | Method for preparing 1, 4-cyclohexanediamine by adding hydrogen continuously at high pressure | |
| CN104326927A (en) | Preparation method of 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol sulfate | |
| CN113754585B (en) | Novel tetrahydroisoquinoline compound and preparation method and application thereof | |
| CN103755689A (en) | Preparation method for prucalopride degradation impurities | |
| CN112279776B (en) | Method for synthesizing arformoterol free alkali | |
| CN111732518A (en) | Preparation method of cis-4- [ (2-amino-3, 5-dibromobenzyl) amino ] cyclohexanol | |
| WO2005121066A1 (en) | The preparation method of (1 r,2s)-(-)-ephedrine or its hydrochloride | |
| CN109574983B (en) | Preparation method of rotigotine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170524 |
|
| RJ01 | Rejection of invention patent application after publication |