CN108484484B - Preparation method of 2-oxo-3-ethyl piperidinecarboxylate - Google Patents
Preparation method of 2-oxo-3-ethyl piperidinecarboxylate Download PDFInfo
- Publication number
- CN108484484B CN108484484B CN201810497214.2A CN201810497214A CN108484484B CN 108484484 B CN108484484 B CN 108484484B CN 201810497214 A CN201810497214 A CN 201810497214A CN 108484484 B CN108484484 B CN 108484484B
- Authority
- CN
- China
- Prior art keywords
- oxo
- ethyl
- diethyl malonate
- piperidinecarboxylate
- diethyl
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims abstract description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- DUMNOWYWTAYLJN-UHFFFAOYSA-N ethyl 2-oxopiperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1=O DUMNOWYWTAYLJN-UHFFFAOYSA-N 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 2-oxo-3-ethyl piperidine formate Chemical compound 0.000 claims abstract description 9
- YJJLOESDBPRZIP-UHFFFAOYSA-N diethyl 2-(2-cyanoethyl)propanedioate Chemical compound CCOC(=O)C(CCC#N)C(=O)OCC YJJLOESDBPRZIP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 5
- 239000010941 cobalt Substances 0.000 claims abstract description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 11
- 239000003426 co-catalyst Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000000498 cooling water Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-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
- 238000010521 absorption reaction 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
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 2
- 229960003987 melatonin Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000036995 brain health Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810497214.2A CN108484484B (en) | 2018-05-22 | 2018-05-22 | Preparation method of 2-oxo-3-ethyl piperidinecarboxylate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810497214.2A CN108484484B (en) | 2018-05-22 | 2018-05-22 | Preparation method of 2-oxo-3-ethyl piperidinecarboxylate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108484484A CN108484484A (en) | 2018-09-04 |
CN108484484B true CN108484484B (en) | 2021-01-05 |
Family
ID=63351541
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810497214.2A Active CN108484484B (en) | 2018-05-22 | 2018-05-22 | Preparation method of 2-oxo-3-ethyl piperidinecarboxylate |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108484484B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115010623A (en) * | 2022-06-29 | 2022-09-06 | 福建科宏生物工程股份有限公司 | Preparation method of 2-cyanoethyl diethyl malonate |
-
2018
- 2018-05-22 CN CN201810497214.2A patent/CN108484484B/en active Active
Non-Patent Citations (4)
Title |
---|
N-乙酰基-5-甲氧基色胺的化学合成;胡松林等;《化学世界》;20161125(第11期);第699-701页 * |
Studies toworad (-)-Gymnodimine: Concise Routes to the Spirocyclic and Tetrahydrofuran Moieties;Ju Yang,et al.;《Organic Letters》;20000225;第2卷(第6期);第763-766页 * |
色胺;周锡瑞等;《中国医药工业杂志》;19840927(第9期);第28-30页 * |
褪黑激素的合成工艺改进;李云等;《中国医药工业杂志》;19990821;第30卷(第8期);第340-341页 * |
Also Published As
Publication number | Publication date |
---|---|
CN108484484A (en) | 2018-09-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN111630049B (en) | Process for preparing 2- (5-methoxyisochroman-1-yl) -4, 5-dihydro-1H-imidazole and bisulphates thereof | |
WO2011113228A1 (en) | A process for preparing guaiacol glycidyl | |
CN108484484B (en) | Preparation method of 2-oxo-3-ethyl piperidinecarboxylate | |
CN105601496B (en) | A kind of preparation method of 3,4 dimethoxy benzenpropanoic acid | |
CN112624923B (en) | Preparation method of 4-methoxy methyl acetoacetate | |
CN112679363B (en) | Method for preparing pentazocine intermediate | |
CN112479853B (en) | Preparation method of D-2-chloropropionyl chloride and D-2-chloropropionyl chloride | |
CN107382883A (en) | The process of N methylhomopiperazins is prepared using 2 halo ethylamine compounds | |
CN111675671A (en) | Preparation method of venlafaxine impurity E | |
CN109265385B (en) | Synthesis process of chiral catalyst | |
CN106673967B (en) | Preparation method of 4- (2-methallyl) -1, 2-benzenediol | |
KR20160077000A (en) | Method for Effective Production and Purification of Anhydrosugar Alcohols | |
CN115466255B (en) | Tropine and synthetic method thereof | |
CN114349635B (en) | Synthesis method of dolutegravir core intermediate | |
CN112125864B (en) | Synthesis method of 1,1 '-diamino-5, 5' -bitetrazole | |
CN112430205B (en) | Preparation method of arylpyrrole compound | |
CN103183632A (en) | Purification method of 3-azabicyclo-octane hydrochloride | |
CN114716341B (en) | Method for preparing dimethenamid by one-pot method | |
CN114478230B (en) | Resolution method of 3-acetyl-2, 2-dimethylcyclopropane carboxylic acid | |
EP2513041A1 (en) | Process for the preparation of o-desmethyl-venlafaxine and salts thereof | |
CN109836373B (en) | Environment-friendly preparation method of vitamin B6 and tail gas recycling method | |
CN106749053B (en) | The preparation method of Lormetazepam rearrangement product | |
CN114105781A (en) | Preparation method of intermediate | |
CN106866402B (en) | Preparation method of (R) -2-hydroxy-4-phenylbutyric acid | |
CN117229136A (en) | Preparation method of azelaic acid |
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 | ||
CB03 | Change of inventor or designer information | ||
CB03 | Change of inventor or designer information |
Inventor after: Yao Husheng Inventor after: Zhao Zhulin Inventor after: Zhang Ming Inventor before: Yao Husheng Inventor before: Zhao Zhulin Inventor before: Zhang Ming Inventor before: Chen Bo |
|
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of 2-oxo-3-piperidine ethyl formate Effective date of registration: 20230512 Granted publication date: 20210105 Pledgee: Industrial Bank Co.,Ltd. Shanghai Minhang sub branch Pledgor: SHANGHAI JINGWEI CHEMICAL TECHNOLOGY Co.,Ltd. Registration number: Y2023310000184 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20210105 Pledgee: Industrial Bank Co.,Ltd. Shanghai Minhang sub branch Pledgor: SHANGHAI JINGWEI CHEMICAL TECHNOLOGY Co.,Ltd. Registration number: Y2023310000184 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of 2-oxo-3-piperidine ethyl formate Granted publication date: 20210105 Pledgee: Industrial Bank Co.,Ltd. Shanghai Minhang sub branch Pledgor: SHANGHAI JINGWEI CHEMICAL TECHNOLOGY Co.,Ltd. Registration number: Y2024310000409 |