DE2151716C3 - Verfahren zur Herstellung von Estern von 2-Aryl-2-dimethylamino-lalkanolen - Google Patents
Verfahren zur Herstellung von Estern von 2-Aryl-2-dimethylamino-lalkanolenInfo
- Publication number
- DE2151716C3 DE2151716C3 DE19712151716 DE2151716A DE2151716C3 DE 2151716 C3 DE2151716 C3 DE 2151716C3 DE 19712151716 DE19712151716 DE 19712151716 DE 2151716 A DE2151716 A DE 2151716A DE 2151716 C3 DE2151716 C3 DE 2151716C3
- Authority
- DE
- Germany
- Prior art keywords
- esters
- hours
- ester
- dimethylamino
- reaction
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001414 amino alcohols Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- -1 amino ester Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- JDCWNZJOVSBOLK-UHFFFAOYSA-N 2-(dimethylamino)-2-phenylbutan-1-ol Chemical compound CCC(CO)(N(C)C)C1=CC=CC=C1 JDCWNZJOVSBOLK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KACHFMOHOPLTNX-UHFFFAOYSA-N Methyl EudesMate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 KACHFMOHOPLTNX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- FSRLGULMGJGKGI-BTJKTKAUSA-N Trimebutine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=CC=1C(CC)(N(C)C)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 FSRLGULMGJGKGI-BTJKTKAUSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- QULRDJFRGVHKLN-UHFFFAOYSA-N ethyl 2-(4-chlorophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Cl)C=C1 QULRDJFRGVHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7108701A FR2131804B1 (enrdf_load_stackoverflow) | 1971-03-12 | 1971-03-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2151716A1 DE2151716A1 (de) | 1972-11-30 |
| DE2151716B2 DE2151716B2 (de) | 1979-01-04 |
| DE2151716C3 true DE2151716C3 (de) | 1979-08-30 |
Family
ID=9073447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712151716 Expired DE2151716C3 (de) | 1971-03-12 | 1971-10-18 | Verfahren zur Herstellung von Estern von 2-Aryl-2-dimethylamino-lalkanolen |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA967977A (enrdf_load_stackoverflow) |
| DE (1) | DE2151716C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2131804B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1342547A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6986901B2 (en) | 2002-07-15 | 2006-01-17 | Warner-Lambert Company Llc | Gastrointestinal compositions |
| CN102276487B (zh) * | 2011-06-29 | 2013-06-12 | 岳阳亚王精细化工有限公司 | 一种曲美布汀的制备方法 |
| CN115093337A (zh) * | 2017-08-01 | 2022-09-23 | 浙江普利药业有限公司 | 一种马来酸曲美布汀晶型及其制备方法 |
| RU2706166C2 (ru) * | 2017-11-20 | 2019-11-14 | Общество С Ограниченной Ответственностью "Валента - Интеллект" | Новые полиморфные формы тримебутина малеата, способ получения и применения |
| RU2770300C2 (ru) * | 2019-10-17 | 2022-04-15 | Общество С Ограниченной Ответственностью "Валента - Интеллект" | Новые полиморфные формы тримебутина малеата, способ получения и применения |
| CN115385806B (zh) * | 2022-07-28 | 2024-04-19 | 山西双雁药业有限公司 | 制备曲美布汀和马来酸曲美布汀的方法 |
-
1971
- 1971-03-12 FR FR7108701A patent/FR2131804B1/fr not_active Expired
- 1971-10-18 DE DE19712151716 patent/DE2151716C3/de not_active Expired
-
1972
- 1972-01-13 GB GB165972A patent/GB1342547A/en not_active Expired
- 1972-03-10 CA CA136,846A patent/CA967977A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2131804A1 (enrdf_load_stackoverflow) | 1972-11-17 |
| GB1342547A (en) | 1974-01-03 |
| FR2131804B1 (enrdf_load_stackoverflow) | 1974-03-22 |
| DE2151716B2 (de) | 1979-01-04 |
| DE2151716A1 (de) | 1972-11-30 |
| CA967977A (en) | 1975-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |