JP2005506355A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005506355A5 JP2005506355A5 JP2003536205A JP2003536205A JP2005506355A5 JP 2005506355 A5 JP2005506355 A5 JP 2005506355A5 JP 2003536205 A JP2003536205 A JP 2003536205A JP 2003536205 A JP2003536205 A JP 2003536205A JP 2005506355 A5 JP2005506355 A5 JP 2005506355A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- solvent
- chloride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 22
- 239000002253 acid Substances 0.000 claims 17
- 239000002904 solvent Substances 0.000 claims 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 8
- -1 trifluoroacetyl compound Chemical class 0.000 claims 8
- 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 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 150000002923 oximes Chemical class 0.000 claims 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 4
- 229940011051 isopropyl acetate Drugs 0.000 claims 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 4
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 claims 4
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000005171 halobenzenes Chemical class 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 2
- 125000005262 alkoxyamine group Chemical group 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 230000009466 transformation Effects 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 0 CCOI*=C(C1CCNCC1)c(cc1)ccc1Br Chemical compound CCOI*=C(C1CCNCC1)c(cc1)ccc1Br 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32956201P | 2001-10-15 | 2001-10-15 | |
| PCT/US2002/032761 WO2003033465A1 (en) | 2001-10-15 | 2002-10-15 | Synthesis of (4-bromophenyl) (4-piperidyl)methanone-(z)-o-ethyloxime and salts |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009119322A Division JP2009173688A (ja) | 2001-10-15 | 2009-05-15 | （４−ブロモフェニル）（４−ピペリジル）メタノン−（ｚ）−ｏ−エチルオキシムおよび塩の合成 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005506355A JP2005506355A (ja) | 2005-03-03 |
| JP2005506355A5 true JP2005506355A5 (enExample) | 2006-01-05 |
Family
ID=23285983
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003536205A Pending JP2005506355A (ja) | 2001-10-15 | 2002-10-15 | （４−ブロモフェニル）（４−ピペリジル）メタノン−（ｚ）−ｏ−エチルオキシムおよび塩の合成 |
| JP2009119322A Withdrawn JP2009173688A (ja) | 2001-10-15 | 2009-05-15 | （４−ブロモフェニル）（４−ピペリジル）メタノン−（ｚ）−ｏ−エチルオキシムおよび塩の合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009119322A Withdrawn JP2009173688A (ja) | 2001-10-15 | 2009-05-15 | （４−ブロモフェニル）（４−ピペリジル）メタノン−（ｚ）−ｏ−エチルオキシムおよび塩の合成 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6914142B2 (enExample) |
| EP (1) | EP1436262A1 (enExample) |
| JP (2) | JP2005506355A (enExample) |
| CN (1) | CN1308308C (enExample) |
| AR (1) | AR036882A1 (enExample) |
| CA (1) | CA2463506C (enExample) |
| MX (1) | MXPA04003478A (enExample) |
| WO (1) | WO2003033465A1 (enExample) |
| ZA (1) | ZA200402068B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6914142B2 (en) * | 2001-10-15 | 2005-07-05 | Schering Corporation | Synthesis of (4-bromopnenyl)(4-piperidyl)methanone-(Z)-O-ethyloxime and salts |
| US10710977B2 (en) * | 2017-02-08 | 2020-07-14 | Nissan Chemical Corporation | Method for producing geometrical isomer of oximino compound |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4408054A (en) * | 1981-11-12 | 1983-10-04 | Hoechst-Roussel Pharmaceuticals Inc. | Oximes of 4-benzoyl-piperidines |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| CN1524527A (zh) | 1999-05-04 | 2004-09-01 | ���鹫˾ | 用作ccr5拮抗剂的哌啶衍生物 |
| US6642385B2 (en) * | 2001-10-15 | 2003-11-04 | Schering Corporation | Synthesis of 4-(piperidyl)(2-pyridyl)methanone-(E)-O-methyloxime and salts |
| US6914142B2 (en) * | 2001-10-15 | 2005-07-05 | Schering Corporation | Synthesis of (4-bromopnenyl)(4-piperidyl)methanone-(Z)-O-ethyloxime and salts |
-
2002
- 2002-10-11 US US10/269,803 patent/US6914142B2/en not_active Expired - Fee Related
- 2002-10-11 AR ARP020103833A patent/AR036882A1/es unknown
- 2002-10-15 MX MXPA04003478A patent/MXPA04003478A/es active IP Right Grant
- 2002-10-15 JP JP2003536205A patent/JP2005506355A/ja active Pending
- 2002-10-15 WO PCT/US2002/032761 patent/WO2003033465A1/en not_active Ceased
- 2002-10-15 EP EP02801697A patent/EP1436262A1/en not_active Withdrawn
- 2002-10-15 CA CA2463506A patent/CA2463506C/en not_active Expired - Fee Related
- 2002-10-15 CN CNB028203720A patent/CN1308308C/zh not_active Expired - Fee Related
-
2004
- 2004-03-15 ZA ZA200402068A patent/ZA200402068B/en unknown
-
2005
- 2005-04-04 US US11/098,642 patent/US7524963B2/en not_active Expired - Fee Related
-
2009
- 2009-05-15 JP JP2009119322A patent/JP2009173688A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Prakash et al. | Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: use in the synthesis of 1, 1-difluoro-1-alkenes | |
| JP5750769B2 (ja) | ２，２−ジフルオロエチルアミンの調製方法 | |
| Suffert et al. | An easy and useful preparation of propynyllithium from (Z/E)-1-bromopropene | |
| IL196234A (en) | Derivative 2-arylic cyclopropane carboxamide optical activity | |
| JP2005506355A5 (enExample) | ||
| US10519085B2 (en) | Process for preparing substituted 2-arylethanols | |
| CA2463506A1 (en) | Synthesis of (4-bromophenyl) (4-piperidyl)methanone-(z)-o-ethyloxime and salts | |
| Zeng et al. | Nickel-, palladium-, and platinum-catalyzed reactions of perfluoro-and polyfluoroalkyl iodides with tetriary amines | |
| EP1347960B1 (en) | Process for preparing (+) trans-4-p-fluorophenyl-3-hydroxymethyl-1 | |
| JPWO1995001323A1 (ja) | 光学活性アミノアルコール誘導体及びその製法 | |
| JP4425632B2 (ja) | ４−（ピペリジル）（２−ピリジル）メタノン−（ｅ）−ｏ−メチルオキシムおよびその塩の合成 | |
| JPH09500626A (ja) | Ｏ−置換ヒドロキシルアンモニウム塩の製法 | |
| JP2001354597A (ja) | シクロプロペン類の製造方法 | |
| JP4163763B2 (ja) | シクロペンタジエン系化合物のアルキル化方法 | |
| CN1155557C (zh) | 特比萘芬盐酸盐的合成 | |
| HU226690B1 (en) | Process for producing fluoxetin | |
| JP4649733B2 (ja) | トリフルオロメチル基含有アセトフェノン化合物の製造方法 | |
| JP2005506357A5 (enExample) | ||
| TWI225056B (en) | Process for preparing tricyclic compounds having antihistaminic activity | |
| JP3905340B2 (ja) | 有機金属化合物の新規調製法 | |
| JP2005501056A5 (enExample) | ||
| HK1048983A1 (zh) | 邻氯甲基苯基二羟乙酸衍生物的制备方法 | |
| CN1222500C (zh) | 联苯－2－羧酸衍生物的制备方法 | |
| JPH0466216B2 (enExample) | ||
| JP4300675B2 (ja) | グリニャール試薬調製法 |