KR840002355A - 엔카이니드의 제조공정 - Google Patents
엔카이니드의 제조공정 Download PDFInfo
- Publication number
- KR840002355A KR840002355A KR1019820005318A KR820005318A KR840002355A KR 840002355 A KR840002355 A KR 840002355A KR 1019820005318 A KR1019820005318 A KR 1019820005318A KR 820005318 A KR820005318 A KR 820005318A KR 840002355 A KR840002355 A KR 840002355A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- until
- methyl
- catalyst
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 7
- 229910052697 platinum Inorganic materials 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- -1 1-methyl-2-piperidyl Chemical group 0.000 claims 2
- CZDIHHFANHXHCA-UHFFFAOYSA-N 4-methoxy-n-phenyl-2-(2-pyridin-2-ylacetyl)benzamide Chemical compound C=1C=CC=NC=1CC(=O)C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1 CZDIHHFANHXHCA-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000001179 sorption measurement Methods 0.000 claims 2
- CITOMGFGTPRDBS-UHFFFAOYSA-N 2-ethyl-n-phenylbenzamide Chemical compound CCC1=CC=CC=C1C(=O)NC1=CC=CC=C1 CITOMGFGTPRDBS-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- BEBIQSRTLZBRRT-UHFFFAOYSA-N lithium;2-methylidenepyridin-1-ide Chemical compound [Li+].[CH2-]C1=CC=CC=N1 BEBIQSRTLZBRRT-UHFFFAOYSA-N 0.000 claims 1
- IHMUJQKXSXXRSK-UHFFFAOYSA-N methyl 2-[(4-methoxybenzoyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(OC)C=C1 IHMUJQKXSXXRSK-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- a) 메틸 N－P－아니소일 안트라닐레이트(하기 구조식 Ⅲ)을 2－피콜릴리튬과 반응시켜 2－(2－피리딜아세틸)－P－아니스아닐리드(하기 구조식 Ⅱ)을 얻어내는 것; b) (하기 구조식 Ⅱ)의 산부가염을 형성하는 것과 상기 염을 백금 및 팔라듐 촉매, 과량의 포름알데하이드 존재하에서 수소와 반응시키는 것을 포함하는 것을 특징으로 하는 4－메톡시－2′－2－(1－메틸－2－피페리딜)에틸 벤즈－아닐리드(하기 구조식 Ⅰ)의 제조공정.
- a) 수소당량이 3이 될때까지 백금촉매존재하에서, 빙초산의 2－(2－피리딜아세틸)－P－아니스아닐리드의 산부가염을 수소화하는 것; b) 백금촉매를 팔라듐상 탄소촉매로 대치하여 2당량이상의 수소가 흡착될때까지 수소화를 계속하는 것; c) 과량의 37%포르말린을 가하며 수소흡착이 끝날때까지 수소화를 계속하는 것을 포함하는 4－메톡시－2′－[2－(1－메틸－2－피페리딜)에틸]벤즈－아닐리드를 제조하는 공정.
- 제2항의 공정에 있어서, 2－(2－피리딜아세틸)－p－아니스아닐리드의 하이드로클로라이드염을 정압에서 빙초산에서, 실은에서, 3당량의 수소가 gmqckrehlfEoRK지 수소의 존재하에서 백금촉매로써 교반하는 것; 백금촉매를 여과, 제거하며 건조 팔라듐상탄소촉매를 여액에다 첨가한후 본 반응혼합물을 수소존재하에 55°－95°에서 2이상의 당량이 흡착될 때까지 가하는 것;혼합물을 25° 또는 그 이하로 냉각시켜 과량의 27%포르말린을 반응혼합물에 주사한후, 20°－40°에서, 수소흡착이 모두 중단될때까지 교반하는 것; 을 포함하는 4－메톡시－2′－[2－(1－메틸－2－피페리딜)에틸]벤즈아닐리드를 제조하는 공정.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US330298 | 1981-12-14 | ||
| US06/330,298 US4394507A (en) | 1981-12-14 | 1981-12-14 | Process for production of encainide |
| US330,298 | 1981-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002355A true KR840002355A (ko) | 1984-06-25 |
| KR890000419B1 KR890000419B1 (ko) | 1989-03-17 |
Family
ID=23289147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205318A KR890000419B1 (ko) | 1981-12-14 | 1982-11-25 | 엔카이니드의 제조 방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4394507A (ko) |
| JP (1) | JPS6058231B2 (ko) |
| KR (1) | KR890000419B1 (ko) |
| AT (1) | AT378182B (ko) |
| CA (1) | CA1213282A (ko) |
| CH (1) | CH655101A5 (ko) |
| DK (1) | DK156648C (ko) |
| ES (2) | ES517996A0 (ko) |
| FI (1) | FI76561C (ko) |
| GR (1) | GR77107B (ko) |
| HU (1) | HU186190B (ko) |
| IT (1) | IT1149399B (ko) |
| NL (1) | NL8204775A (ko) |
| PT (1) | PT75980B (ko) |
| SE (1) | SE454442B (ko) |
| YU (1) | YU44035B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675409A (en) * | 1986-02-25 | 1987-06-23 | Bristol-Myers Company | Process for the preparation of encainide |
| US4800226A (en) * | 1986-02-25 | 1989-01-24 | Bristol-Myers Company | Process intermediate for the preparation of encainide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2317303A (en) * | 1940-12-07 | 1943-04-20 | Merck & Co Inc | Heterocyclic nitrogen containing compounds, and processes for making the same |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
| CA961038A (en) * | 1971-03-03 | 1975-01-14 | Joseph L. Minielli | Substituted piperidines |
| US4064254A (en) * | 1971-03-03 | 1977-12-20 | Mead Johnson & Company | Substituted piperidines therapeutic process and compositions |
| US4000143A (en) * | 1971-03-03 | 1976-12-28 | Mead Johnson & Company | Substituted piperidines |
| SE7607114L (sv) * | 1976-06-22 | 1977-12-23 | Bofors Ab | Sett att framstella hydrokloriden av n-metylpiperidin-2-karbonsyra-2,6-xyllidid |
-
1981
- 1981-12-14 US US06/330,298 patent/US4394507A/en not_active Expired - Fee Related
-
1982
- 1982-11-18 GR GR69848A patent/GR77107B/el unknown
- 1982-11-22 CA CA000416079A patent/CA1213282A/en not_active Expired
- 1982-11-25 KR KR8205318A patent/KR890000419B1/ko active
- 1982-12-02 IT IT49608/82A patent/IT1149399B/it active
- 1982-12-07 YU YU2710/82A patent/YU44035B/xx unknown
- 1982-12-07 ES ES517996A patent/ES517996A0/es active Granted
- 1982-12-09 JP JP57214747A patent/JPS6058231B2/ja not_active Expired
- 1982-12-09 NL NL8204775A patent/NL8204775A/nl unknown
- 1982-12-09 FI FI824234A patent/FI76561C/fi not_active IP Right Cessation
- 1982-12-10 DK DK551582A patent/DK156648C/da not_active IP Right Cessation
- 1982-12-13 PT PT75980A patent/PT75980B/pt not_active IP Right Cessation
- 1982-12-13 SE SE8207112A patent/SE454442B/sv not_active IP Right Cessation
- 1982-12-13 HU HU824018A patent/HU186190B/hu not_active IP Right Cessation
- 1982-12-13 CH CH7245/82A patent/CH655101A5/de not_active IP Right Cessation
- 1982-12-14 AT AT0454082A patent/AT378182B/de not_active IP Right Cessation
-
1984
- 1984-03-01 ES ES530218A patent/ES530218A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| YU271082A (en) | 1985-03-20 |
| SE454442B (sv) | 1988-05-02 |
| SE8207112D0 (sv) | 1982-12-13 |
| DK156648B (da) | 1989-09-18 |
| CA1213282A (en) | 1986-10-28 |
| ES8506274A1 (es) | 1985-07-01 |
| ATA454082A (de) | 1984-11-15 |
| CH655101A5 (de) | 1986-03-27 |
| FI824234L (fi) | 1983-06-15 |
| US4394507A (en) | 1983-07-19 |
| YU44035B (en) | 1990-02-28 |
| IT8249608A0 (it) | 1982-12-02 |
| ES530218A0 (es) | 1985-07-01 |
| FI76561C (fi) | 1988-11-10 |
| GR77107B (ko) | 1984-09-06 |
| ES8405767A1 (es) | 1984-06-16 |
| PT75980A (en) | 1983-01-01 |
| JPS58105963A (ja) | 1983-06-24 |
| FI76561B (fi) | 1988-07-29 |
| SE8207112L (sv) | 1983-06-15 |
| AT378182B (de) | 1985-06-25 |
| IT1149399B (it) | 1986-12-03 |
| PT75980B (en) | 1985-12-20 |
| NL8204775A (nl) | 1983-07-01 |
| KR890000419B1 (ko) | 1989-03-17 |
| FI824234A0 (fi) | 1982-12-09 |
| HU186190B (en) | 1985-06-28 |
| DK551582A (da) | 1983-06-15 |
| ES517996A0 (es) | 1984-06-16 |
| DK156648C (da) | 1990-03-05 |
| JPS6058231B2 (ja) | 1985-12-19 |
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