CN104230853A - Preparation method of (p-methylphenyl) methylamine-N-morpholinoethyl hydrochloride - Google Patents
Preparation method of (p-methylphenyl) methylamine-N-morpholinoethyl hydrochloride Download PDFInfo
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- CN104230853A CN104230853A CN201410405918.4A CN201410405918A CN104230853A CN 104230853 A CN104230853 A CN 104230853A CN 201410405918 A CN201410405918 A CN 201410405918A CN 104230853 A CN104230853 A CN 104230853A
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- 238000002360 preparation method Methods 0.000 title abstract description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006722 reduction reaction Methods 0.000 claims abstract description 12
- 238000005917 acylation reaction Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 6
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000007344 nucleophilic reaction Methods 0.000 claims description 9
- SHJAQDKRNKFLKG-UHFFFAOYSA-N Cl.C(C)N1CCOCC1.CC1=CC=C(C=C1)NC Chemical compound Cl.C(C)N1CCOCC1.CC1=CC=C(C=C1)NC SHJAQDKRNKFLKG-UHFFFAOYSA-N 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 229940125898 compound 5 Drugs 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 15
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 229960001701 chloroform Drugs 0.000 claims 2
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 229910000085 borane Inorganic materials 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 230000010933 acylation Effects 0.000 abstract 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 7
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- -1 Compound (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride Chemical class 0.000 description 4
- ALIMFNFGBSRNIO-UHFFFAOYSA-N C(C)N1CCOCC1.CC1=CC=C(C=C1)NC Chemical compound C(C)N1CCOCC1.CC1=CC=C(C=C1)NC ALIMFNFGBSRNIO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses a preparation method of (p-methylphenyl) methylamine-N-morpholinoethyl hydrochloride. The preparation method comprises the following step: by using 4-methylbenzylamine as an initial raw material, carrying out acylation, nucleophilic substitution, reduction and hydrochloride formation to obtain a targeted product. The compound is an important medical intermediate.
Description
Technical field
The present invention relates to a kind of novel processing step of medicine intermediate, particularly a kind of preparation method of (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride.
Technical background
Compound (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride, structural formula is:
This compound (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride and relevant derivative have widespread use in pharmaceutical chemistry and organic synthesis.The synthesis of (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride is comparatively difficult at present.Therefore, need exploitation raw material to be easy to get, easy to operate, reaction is easy to control, the synthetic method that overall yield is suitable.
Summary of the invention
The invention discloses the method that one prepares (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride, with 4-methylbenzylamine for starting raw material, obtain target product 5 through acidylate, nucleophilic, reduction, one-tenth hydrochloride, synthetic route as shown in Figure 1.Synthesis step is as follows:
(1) with 4-methylbenzylamine for starting raw material, obtain 2 through acylation reaction;
(2) carry out nucleophilic reaction 2 with morpholine, obtain 3;
(3) carry out reduction reaction 3 and obtain 4;
(3) carry out into hydrochloride 4 and be obtained by reacting target product 5,
One preferred embodiment in, the reagent that described acylation reaction prepares compound 2 used is selected from chloroacetyl chloride; The alkali that described nucleophilic reaction prepares compound 3 used is selected from salt of wormwood; The reductive agent used that described reduction reaction prepares compound 4 used is selected from Lithium Aluminium Hydride; The reagent that described salt-forming reaction prepares compound 5 used is selected from hydrogenchloride.
One preferred embodiment in, the solvent that described acylation reaction prepares compound 2 used is selected from methylene dichloride; The solvent that described nucleophilic reaction prepares compound 3 used is selected from tetrahydrofuran (THF); The solvent that described reduction reaction prepares compound 4 used is selected from tetrahydrofuran (THF); Compound 5 solvent selected from methanol used is prepared in described one-tenth hydrochloride reaction.
One preferred embodiment in, it is 0 DEG C that described acylation reaction prepares compound 2 temperature of reaction used; Described nucleophilic reaction prepares the reflux temperature that compound 3 temperature used is solvent; It is 0 DEG C that described reduction reaction prepares compound 4 temperature used; Described one-tenth hydrochloride reaction prepare compound 5 used be room temperature.
The present invention relates to the preparation method of one (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride, there is no other Patents bibliographical informations at present.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of compound (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride.
The present invention is further described by the following embodiment, and these descriptions are not be further limited content of the present invention.One skilled in the art will understand that the equivalent replacement that technical characteristic of the present invention is done, or improve accordingly, still belong within protection scope of the present invention.
Specific embodiment mode
Embodiment 1
(1) synthesis of (the chloro-N-acetamido of 2-)-4-methyl benzene methanamine
15g4-methylbenzylamine is joined in 120ml methylene dichloride, is cooled to 0 DEG C, drip chloroacetyl chloride, stir 2 hours, add water to extract, separatory, drying, concentrated, residuum upper prop is separated and obtains 17g (the chloro-N-acetamido of 2-)-4-methyl benzene methanamine.
(2) synthesis of (2-morpholine-N-acetamido)-4-methyl benzene methanamine
16g (the chloro-N-acetamido of 2-)-4-methyl benzene methanamine is joined in 150ml tetrahydrofuran (THF), add 6g salt of wormwood, reheat backflow to spend the night, be cooled to room temperature, concentrated, then add water and methylene dichloride, extraction separatory, collect organic phase, separatory, drying, concentrated, on residuum, silicagel column is separated to obtain 19g (2-morpholine-N-acetamido)-4-methyl benzene methanamine.
(3) synthesis of (p-methylphenyl) methylamine-N-ethylmorpholine
18g (2-morpholine-N-acetamido)-4-methyl benzene methanamine is joined in 120ml tetrahydrofuran (THF), is cooled to 0 DEG C, slowly adds 6g Lithium Aluminium Hydride, 0 DEG C is stirred 5 hours, adds water, filters, filtrate concentrates, and obtains 13g (p-methylphenyl) methylamine-N-ethylmorpholine.
(4) synthesis of (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride
12g (p-methylphenyl) methylamine-N-ethylmorpholine is joined in 100ml methyl alcohol, and logical hydrogenchloride is to saturated, and stirring at room temperature 24 hours, concentrating under reduced pressure obtains 15.6g (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride.
Claims (6)
1. prepare a method for (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride, with 4-methylbenzylamine for starting raw material, obtain target product 5 through acidylate, nucleophilic, reduction, one-tenth hydrochloride, synthetic route is as follows.
2. method according to claim 1, it is characterized by 4 described step reactions is,
(1) with 4-methylbenzylamine for starting raw material, obtain 2 through acylation reaction;
(2) carry out nucleophilic reaction 2 with morpholine, obtain 3;
(3) carry out reduction reaction 3 and obtain 4;
(3) carry out into hydrochloride 4 and be obtained by reacting target product 5,
3. according to the method for claim 1-2, it is characterized in that, the reagent that described acylation reaction prepares compound 2 used is selected from chloroacetyl chloride; Described nucleophilic reaction is prepared compound 3 alkali used and is selected from the mixture of one or more in sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, salt of wormwood, sodium hydride, triethylamine, sodium bicarbonate, pyridine, triisopropylamine, saleratus, sodium methylate, sodium ethylate; Described reduction substitution reaction is prepared compound 4 reductive agent used used and is selected from the mixture of one or more in sodium borohydride, POTASSIUM BOROHYDRIDE, lithium borohydride, sodium cyanoborohydride, lithium aluminium hydride, borine; The reagent that described oxidizing reaction prepares compound 5 used is selected from hydrogenchloride.
4. according to the method for claim 1-2, it is characterized in that, described acylation reaction is prepared compound 2 solvent used and is selected from tetrahydrofuran (THF), methylene dichloride, toluene, o-Xylol, p-Xylol, m-xylene, N, the mixture of one or more in dinethylformamide, N,N-dimethylacetamide; Described nucleophilic reaction is prepared compound 3 solvent used and is selected from methylene dichloride, trichloromethane, ethyl acetate, tetrahydrofuran (THF), toluene, tetrahydrofuran (THF), toluene, o-Xylol, p-Xylol, m-xylene, N, the mixture of one or more in dinethylformamide, N,N-dimethylacetamide; Described reduction reaction prepares compound 4 solvent selected from methanol used, ethanol, n-propyl alcohol, Virahol, tetrahydrofuran (THF), methylene dichloride, toluene, o-Xylol, p-Xylol, m-xylene, N, the mixture of one or more in dinethylformamide, N,N-dimethylacetamide; Compound 5 solvent selected from methanol used, ethanol, n-propyl alcohol, Virahol, tetrahydrofuran (THF), methylene dichloride, trichloromethane, ethyl acetate, toluene, o-Xylol, p-Xylol, m-xylene, N are prepared in described salt-forming reaction, the mixture of one or more in dinethylformamide, N,N-dimethylacetamide.
5. according to the method for claim 1-2, it is characterized in that, described acylation reaction prepares the reflux temperature that compound 2 temperature of reaction used is 0 DEG C ~ solvent; Described nucleophilic reaction prepares the reflux temperature that compound 3 temperature used is 0 DEG C ~ solvent; It is 0 DEG C ~ room temperature that described reduction reaction prepares compound 4 temperature used; Described one-tenth hydrochloride reaction prepare compound 5 used be 0 DEG C ~ room temperature.
6. according to the method for claim 1-2, it is characterized in that, it is 0 DEG C that described acylation reaction prepares compound 2 temperature of reaction used; Described nucleophilic reaction prepares the reflux temperature that compound 3 temperature used is solvent; It is room temperature that described reduction reaction prepares compound 4 temperature used; Described one-tenth hydrochloride reaction prepare compound 5 used be 0 DEG C.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410405918.4A CN104230853B (en) | 2014-08-18 | 2014-08-18 | A kind of preparation method of (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride |
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| CN201410405918.4A CN104230853B (en) | 2014-08-18 | 2014-08-18 | A kind of preparation method of (p-methylphenyl) methylamine-N-ethylmorpholine hydrochloride |
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| CN104230853B CN104230853B (en) | 2016-04-13 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106854188A (en) * | 2015-12-08 | 2017-06-16 | 湖南华腾制药有限公司 | A kind of preparation method of morpholine derivative |
| CN107033105A (en) * | 2017-06-01 | 2017-08-11 | 湖南华腾制药有限公司 | A kind of preparation method of morpholino ethylamine hydrochloride |
| CN107162986A (en) * | 2017-05-31 | 2017-09-15 | 湖南华腾制药有限公司 | A kind of preparation method of the pyrimidine derivatives containing morpholinyl |
| CN107778269A (en) * | 2016-08-30 | 2018-03-09 | 湖南华腾制药有限公司 | A kind of preparation method of morpholine kind compound |
| CN107778267A (en) * | 2016-08-29 | 2018-03-09 | 湖南华腾制药有限公司 | A kind of synthetic method of morpholine derivative |
| CN107778268A (en) * | 2016-08-29 | 2018-03-09 | 湖南华腾制药有限公司 | A kind of preparation method of nitrogenous oxygen organic compound |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106854188A (en) * | 2015-12-08 | 2017-06-16 | 湖南华腾制药有限公司 | A kind of preparation method of morpholine derivative |
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| CN107033105A (en) * | 2017-06-01 | 2017-08-11 | 湖南华腾制药有限公司 | A kind of preparation method of morpholino ethylamine hydrochloride |
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Denomination of invention: Preparation method of (p-methylphenyl) methylamine-N-morpholinoethyl hydrochloride Effective date of registration: 20200318 Granted publication date: 20160413 Pledgee: Bank of Changsha Limited by Share Ltd science and Technology Branch Pledgor: HUNAN HUATENG PHARMACEUTICAL Co.,Ltd. Registration number: Y2020980000827 |