IE59681B1 - New process for the synthesis of N-amino-3-azabicyclo[3.30]octane - Google Patents
New process for the synthesis of N-amino-3-azabicyclo[3.30]octaneInfo
- Publication number
- IE59681B1 IE59681B1 IE148887A IE148887A IE59681B1 IE 59681 B1 IE59681 B1 IE 59681B1 IE 148887 A IE148887 A IE 148887A IE 148887 A IE148887 A IE 148887A IE 59681 B1 IE59681 B1 IE 59681B1
- Authority
- IE
- Ireland
- Prior art keywords
- azabicyclo
- octane
- amino
- monochloroamine
- medium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 26
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 17
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 15
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000243 solution Substances 0.000 claims abstract description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims abstract description 20
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 10
- 239000012429 reaction media Substances 0.000 claims abstract description 10
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 235000019270 ammonium chloride Nutrition 0.000 claims abstract description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims abstract description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 230000002051 biphasic effect Effects 0.000 claims description 5
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 abstract description 15
- FJYWNYLUZBMVKI-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-amine Chemical compound C1CCC2CN(N)CC21 FJYWNYLUZBMVKI-UHFFFAOYSA-N 0.000 abstract description 5
- 238000004064 recycling Methods 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 description 8
- 239000002609 medium Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- -1 bicyclic amine Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8701334A FR2610321B1 (fr) | 1987-02-04 | 1987-02-04 | Nouveau procede de synthese du n-amino aza-3 bicyclo (3, 3, 0) octane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE871488L IE871488L (en) | 1988-08-04 |
| IE59681B1 true IE59681B1 (en) | 1994-03-23 |
Family
ID=9347573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE148887A IE59681B1 (en) | 1987-02-04 | 1987-06-05 | New process for the synthesis of N-amino-3-azabicyclo[3.30]octane |
Country Status (13)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2769016B1 (fr) | 1997-09-30 | 1999-10-29 | Adir | Procede de synthese de chloramine haute teneur |
| FR2864078B1 (fr) | 2003-12-17 | 2006-02-10 | Isochem Sa | Procede de synthese en continu de monoalkyl hydrazines a groupe alkyle fonctionnalise |
| FR2864081B1 (fr) | 2003-12-17 | 2006-04-28 | Isochem Sa | Procede de synthese de derives de cycloalkyl-hydrazines exocycliques et de derives d'heterocycloalkyl-hydrazines exocycliques. |
| US20080156740A1 (en) * | 2006-12-29 | 2008-07-03 | Amit Gupta | Method for producing a stable oxidizing biocide |
| CN101307019B (zh) * | 2008-04-28 | 2010-10-27 | 宁波九胜创新医药科技有限公司 | N-氨基-3-氮杂双环[3,3,0]辛烷盐酸盐的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1449404A (en) * | 1973-03-30 | 1976-09-15 | Science Union & Cie | N-arylsulphonyl urea derivatives |
| YU40105B (en) * | 1973-07-04 | 1985-08-31 | Science Union & Cie | Process for the manufacture of n-arylsulfonyl-n'-(aza-3-bicycloalyl)-carbamides |
| FR2540110B1 (fr) * | 1983-02-02 | 1985-07-05 | Adir | Nouveau procede de fabrication industrielle de n-nitroso azabicycloalcanes |
-
1987
- 1987-02-04 FR FR8701334A patent/FR2610321B1/fr not_active Expired
- 1987-06-05 IE IE148887A patent/IE59681B1/en not_active IP Right Cessation
- 1987-06-12 DE DE8787108477T patent/DE3765925D1/de not_active Expired - Lifetime
- 1987-06-12 AT AT87108477T patent/ATE57914T1/de not_active IP Right Cessation
- 1987-06-12 EP EP87108477A patent/EP0277267B1/fr not_active Expired - Lifetime
- 1987-06-15 AR AR87307860A patent/AR243160A1/es active
- 1987-06-15 DK DK303987A patent/DK169669B1/da not_active IP Right Cessation
- 1987-06-15 CA CA000539646A patent/CA1283420C/fr not_active Expired - Lifetime
- 1987-06-16 AU AU74260/87A patent/AU591784B2/en not_active Expired
- 1987-06-23 ZA ZA874526A patent/ZA874526B/xx unknown
- 1987-06-30 PT PT85211A patent/PT85211B/pt unknown
- 1987-07-06 JP JP62167147A patent/JPS63196565A/ja active Granted
- 1987-09-14 ES ES8702644A patent/ES2005012A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU7426087A (en) | 1988-08-11 |
| EP0277267A1 (fr) | 1988-08-10 |
| EP0277267B1 (fr) | 1990-10-31 |
| FR2610321A1 (fr) | 1988-08-05 |
| JPH0427233B2 (enrdf_load_html_response) | 1992-05-11 |
| CA1283420C (fr) | 1991-04-23 |
| ATE57914T1 (de) | 1990-11-15 |
| DK303987D0 (da) | 1987-06-15 |
| ZA874526B (en) | 1987-12-29 |
| FR2610321B1 (fr) | 1989-04-07 |
| ES2005012A6 (es) | 1989-02-16 |
| DK303987A (da) | 1988-08-05 |
| DE3765925D1 (de) | 1990-12-06 |
| AU591784B2 (en) | 1989-12-14 |
| DK169669B1 (da) | 1995-01-09 |
| PT85211B (pt) | 1990-11-20 |
| PT85211A (fr) | 1987-07-01 |
| JPS63196565A (ja) | 1988-08-15 |
| AR243160A1 (es) | 1993-07-30 |
| IE871488L (en) | 1988-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |