ES2388622T3 - Procedimiento para la preparación de compuestos de 3,7-diaza-biciclo[3.3.1]nonano - Google Patents
Procedimiento para la preparación de compuestos de 3,7-diaza-biciclo[3.3.1]nonano Download PDFInfo
- Publication number
- ES2388622T3 ES2388622T3 ES09777909T ES09777909T ES2388622T3 ES 2388622 T3 ES2388622 T3 ES 2388622T3 ES 09777909 T ES09777909 T ES 09777909T ES 09777909 T ES09777909 T ES 09777909T ES 2388622 T3 ES2388622 T3 ES 2388622T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- reaction
- alkyl
- alcohol
- carried out
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- -1 dicarboxylic acid ester Chemical class 0.000 claims abstract description 10
- 238000002955 isolation Methods 0.000 claims abstract description 10
- 239000013067 intermediate product Substances 0.000 claims abstract description 9
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 8
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 238000010533 azeotropic distillation Methods 0.000 claims abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- 239000001273 butane Substances 0.000 description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008038376A DE102008038376A1 (de) | 2008-08-19 | 2008-08-19 | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
| DE102008038376 | 2008-08-19 | ||
| PCT/EP2009/005937 WO2010020383A1 (de) | 2008-08-19 | 2009-08-17 | Verfarhen zur herstellung von 3,7-diaza-bicyclo[3.3.1]nonan-verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2388622T3 true ES2388622T3 (es) | 2012-10-17 |
Family
ID=41278731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09777909T Active ES2388622T3 (es) | 2008-08-19 | 2009-08-17 | Procedimiento para la preparación de compuestos de 3,7-diaza-biciclo[3.3.1]nonano |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8293910B2 (enExample) |
| EP (1) | EP2318409B1 (enExample) |
| JP (1) | JP5592370B2 (enExample) |
| DE (1) | DE102008038376A1 (enExample) |
| ES (1) | ES2388622T3 (enExample) |
| WO (1) | WO2010020383A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005027619A1 (de) * | 2005-06-15 | 2006-12-28 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
| DE102008045207A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
| DE102008064009A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Ltd. | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Metall-Komplexen |
| CN102875550B (zh) * | 2011-07-12 | 2016-01-06 | 常州合全药业有限公司 | 1,3,7-三取代-3,7-二氮杂双环[3,3,1]壬烷衍生物及制备方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1182143A (en) * | 1966-03-01 | 1970-02-25 | United States Borax Chem | Bleaching Compositions and Methods. |
| US4414127A (en) * | 1981-07-06 | 1983-11-08 | Syntex (U.S.A.) Inc. | Contact lens cleaning solutions |
| GR76237B (enExample) | 1981-08-08 | 1984-08-04 | Procter & Gamble | |
| US4481129A (en) | 1981-12-23 | 1984-11-06 | Lever Brothers Company | Bleach compositions |
| GB8329762D0 (en) | 1983-11-08 | 1983-12-14 | Unilever Plc | Manganese adjuncts |
| GB8405189D0 (en) | 1984-02-28 | 1984-04-04 | Interox Chemicals Ltd | Peroxide activation |
| US4728455A (en) | 1986-03-07 | 1988-03-01 | Lever Brothers Company | Detergent bleach compositions, bleaching agents and bleach activators |
| BR9507984A (pt) | 1994-06-13 | 1997-11-18 | Unilever Nv | Catalisador de alvejamento e de oxidação e composição alvejante |
| DE4443177A1 (de) | 1994-12-05 | 1996-06-13 | Henkel Kgaa | Aktivatormischungen für anorganische Perverbindungen |
| US6734155B1 (en) * | 1997-07-09 | 2004-05-11 | The Procter & Gamble Company | Cleaning compositions comprising an oxidoreductase |
| CA2248476A1 (en) | 1997-10-01 | 1999-04-01 | Unilever Plc | Bleach activation |
| DE19909546C1 (de) | 1999-03-04 | 2000-06-29 | Consortium Elektrochem Ind | Mehrkomponentensystem zur enzymkatalysierten Oxidation von Substraten sowie Verfahren zur enzymkatalysierten Oxidation |
| GB9930422D0 (en) | 1999-12-22 | 2000-02-16 | Unilever Plc | Bleach catalysts |
| GB0030673D0 (en) | 2000-12-15 | 2001-01-31 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
| GB0104980D0 (en) | 2001-02-28 | 2001-04-18 | Unilever Plc | Liquid cleaning compositions and their use |
| CA2472189A1 (en) | 2002-02-28 | 2003-09-04 | Unilever Plc | Bleach catalyst enhancement |
| EP1523482A1 (en) | 2002-06-06 | 2005-04-20 | Unilever N.V. | Ligand and complex for catalytically bleaching a substrate |
| DE10304131A1 (de) | 2003-02-03 | 2004-08-05 | Clariant Gmbh | Verwendung von Übergangsmetallkomplexen als Bleichkatalysatoren |
| DE10345273A1 (de) | 2003-09-30 | 2005-04-21 | Clariant Gmbh | Verwendung von Übergangsmetallkomplexen mit Lactamliganden als Bleichkatalysatoren |
| GB0325432D0 (en) * | 2003-10-31 | 2003-12-03 | Unilever Plc | Ligand and complex for catalytically bleaching a substrate |
| GB0411304D0 (en) | 2004-05-21 | 2004-06-23 | Fellows Adrian N | An antimicrobial composition |
| DE102005027619A1 (de) * | 2005-06-15 | 2006-12-28 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Verbindungen |
| DE102008045207A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Limited | Bleichkatalysatormischungen bestehend aus Mangansalzen und Oxalsäure oder deren Salze |
| DE102008045215A1 (de) * | 2008-08-30 | 2010-03-04 | Clariant International Ltd. | Verwendung von Mangan-Oxalatenn als Bleichkatalysatoren |
| DE102008064009A1 (de) * | 2008-12-19 | 2010-06-24 | Clariant International Ltd. | Verfahren zur Herstellung von 3,7-Diaza-bicyclo[3.3.1]nonan-Metall-Komplexen |
-
2008
- 2008-08-19 DE DE102008038376A patent/DE102008038376A1/de not_active Withdrawn
-
2009
- 2009-08-17 US US13/059,470 patent/US8293910B2/en active Active
- 2009-08-17 WO PCT/EP2009/005937 patent/WO2010020383A1/de not_active Ceased
- 2009-08-17 EP EP09777909A patent/EP2318409B1/de active Active
- 2009-08-17 JP JP2011523343A patent/JP5592370B2/ja active Active
- 2009-08-17 ES ES09777909T patent/ES2388622T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20110152528A1 (en) | 2011-06-23 |
| DE102008038376A1 (de) | 2010-02-25 |
| JP2012500238A (ja) | 2012-01-05 |
| JP5592370B2 (ja) | 2014-09-17 |
| WO2010020383A1 (de) | 2010-02-25 |
| EP2318409B1 (de) | 2012-07-11 |
| EP2318409A1 (de) | 2011-05-11 |
| US8293910B2 (en) | 2012-10-23 |
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