CN102060733B - (7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 - Google Patents
(7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 Download PDFInfo
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- CN102060733B CN102060733B CN201010590808.1A CN201010590808A CN102060733B CN 102060733 B CN102060733 B CN 102060733B CN 201010590808 A CN201010590808 A CN 201010590808A CN 102060733 B CN102060733 B CN 102060733B
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- methoxyl
- methoxyl group
- alpha
- dihydro
- naphthyl
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- 238000000034 method Methods 0.000 title claims abstract description 13
- MGJHVZKRAOYORH-UHFFFAOYSA-N 2-(7-methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile Chemical compound C1CC=C(CC#N)C2=CC(OC)=CC=C21 MGJHVZKRAOYORH-UHFFFAOYSA-N 0.000 title abstract description 8
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 20
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000019257 ammonium acetate Nutrition 0.000 claims abstract description 14
- 239000005695 Ammonium acetate Substances 0.000 claims abstract description 10
- 229940043376 ammonium acetate Drugs 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000003053 piperidines Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 229960002629 agomelatine Drugs 0.000 abstract description 12
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- -1 (7-methoxy-1-naphthyl) ethyl Chemical group 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 230000001519 thymoleptic effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 3
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 3
- OYEXEQFKIPJKJK-UHFFFAOYSA-N 2-(cyclohexen-1-yl)acetonitrile Chemical compound N#CCC1=CCCCC1 OYEXEQFKIPJKJK-UHFFFAOYSA-N 0.000 description 2
- MCXUFDVBPBAWQQ-UHFFFAOYSA-M CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1.CCCCCCC([O-])=O Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1.CCCCCCC([O-])=O MCXUFDVBPBAWQQ-UHFFFAOYSA-M 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 238000004176 ammonification Methods 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 206010002869 Anxiety symptoms Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 1
- 229940121723 Melatonin receptor agonist Drugs 0.000 description 1
- 102100024930 Melatonin receptor type 1A Human genes 0.000 description 1
- 101710098568 Melatonin receptor type 1A Proteins 0.000 description 1
- 102100024970 Melatonin receptor type 1B Human genes 0.000 description 1
- 101710098567 Melatonin receptor type 1B Proteins 0.000 description 1
- 238000006680 Reformatsky reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- LNDJVIYUJOJFSO-UHFFFAOYSA-N cyanoacetylene Chemical group C#CC#N LNDJVIYUJOJFSO-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003987 melatonin Drugs 0.000 description 1
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Abstract
Description
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010590808.1A CN102060733B (zh) | 2010-12-06 | 2010-12-06 | (7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010590808.1A CN102060733B (zh) | 2010-12-06 | 2010-12-06 | (7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102060733A CN102060733A (zh) | 2011-05-18 |
| CN102060733B true CN102060733B (zh) | 2014-01-29 |
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| CN201010590808.1A Active CN102060733B (zh) | 2010-12-06 | 2010-12-06 | (7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 |
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| Country | Link |
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| CN (1) | CN102060733B (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1680296A (zh) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | (7－甲氧基－1－萘基)乙腈的新合成方法，及其在阿戈美拉汀的合成中的应用 |
| CN1680295A (zh) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | (7－甲氧基－2－二氢－1－萘基)乙腈的新合成方法，及其在阿戈美拉汀的合成中的应用 |
| CN101723855A (zh) * | 2009-12-03 | 2010-06-09 | 浙江科技学院 | 一种(7-甲氧基-1-萘基)乙腈的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7498465B2 (en) * | 2004-02-13 | 2009-03-03 | Les Laboratoires Servier | Process for the synthesis and crystalline form of agomelatine |
-
2010
- 2010-12-06 CN CN201010590808.1A patent/CN102060733B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1680296A (zh) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | (7－甲氧基－1－萘基)乙腈的新合成方法，及其在阿戈美拉汀的合成中的应用 |
| CN1680295A (zh) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | (7－甲氧基－2－二氢－1－萘基)乙腈的新合成方法，及其在阿戈美拉汀的合成中的应用 |
| CN101723855A (zh) * | 2009-12-03 | 2010-06-09 | 浙江科技学院 | 一种(7-甲氧基-1-萘基)乙腈的合成方法 |
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| Publication number | Publication date |
|---|---|
| CN102060733A (zh) | 2011-05-18 |
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Owner name: WEIHAI DIJIA PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: WEIHAI DISU PHARMACEUTICAL CO., LTD. Effective date: 20140702 Owner name: WEIHAI DISU PHARMACEUTICAL CO., LTD. DISHA PHARMAC Free format text: FORMER OWNER: DISHA PHARMACEUTICAL INDUSTRY GROUP CORP., LTD. Effective date: 20140702 |
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Free format text: CORRECT: ADDRESS; FROM: 264209 WEIHAI, SHANDONG PROVINCE TO: 264400 WEIHAI, SHANDONG PROVINCE |
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Effective date of registration: 20140702 Address after: 264400 No. 46, Guangzhou Road, Wendeng Economic Development Zone, Shandong, Weihai Patentee after: WEIHAI DIJIA PHARMACEUTICAL Co.,Ltd. Patentee after: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee after: DISHA PHARMACEUTICAL GROUP Co.,Ltd. Address before: 264209 No. 196, science and technology road, torch hi tech Industrial Development Zone, Weihai, Shandong, Weihai Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee before: DISHA PHARMACEUTICAL GROUP Co.,Ltd. |
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Effective date of registration: 20160708 Address after: Economic and Technological Development Zone of Shandong Province, Weihai City, Gushan Town, 264209 No. 18 South Road, No. 19 North Road, No. 3 East Road, the west five Patentee after: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Address before: 264400 No. 46, Guangzhou Road, Wendeng Economic Development Zone, Shandong, Weihai Patentee before: WEIHAI DIJIA PHARMACEUTICAL Co.,Ltd. Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. Patentee before: DISHA PHARMACEUTICAL GROUP Co.,Ltd. |
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Effective date of registration: 20200509 Address after: 264205 Guangzhou East Road South and an East Road East, Wendeng economic and Technological Development Zone, Weihai City, Shandong Province Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: Economic and Technological Development Zone of Shandong Province, Weihai City, Gushan Town, 264209 No. 18 South Road, No. 19 North Road, No. 3 East Road, the west five Patentee before: WEIHAI DISU PHARMACEUTICAL Co.,Ltd. |
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Address after: 264205 268 Tianrun Road, Wendeng economic and Technological Development Zone, Weihai, Shandong Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: 264205 Wendeng economic and Technological Development Zone, Weihai City, Shandong Province Patentee before: Dijia Pharmaceutical Group Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 264205 268 Tianrun Road, Wendeng economic and Technological Development Zone, Weihai, Shandong Patentee after: Dijia Pharmaceutical Group Co.,Ltd. Address before: 264205 268 Tianrun Road, Wendeng economic and Technological Development Zone, Weihai, Shandong Patentee before: Dijia Pharmaceutical Group Co.,Ltd. |