ZA200107380B - A process for the preparation of 1,4,7,10-tetraazacyclododecane. - Google Patents
A process for the preparation of 1,4,7,10-tetraazacyclododecane. Download PDFInfo
- Publication number
- ZA200107380B ZA200107380B ZA200107380A ZA200107380A ZA200107380B ZA 200107380 B ZA200107380 B ZA 200107380B ZA 200107380 A ZA200107380 A ZA 200107380A ZA 200107380 A ZA200107380 A ZA 200107380A ZA 200107380 B ZA200107380 B ZA 200107380B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- mol
- iii
- formula
- amounts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 16
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 83
- 238000006243 chemical reaction Methods 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 18
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 16
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 14
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- NYYDZOSYLUOKEM-UHFFFAOYSA-N oxaldehyde;hydrate Chemical compound O.O=CC=O NYYDZOSYLUOKEM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003021 water soluble solvent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000001177 diphosphate Substances 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229940015043 glyoxal Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 150000000921 Gadolinium Chemical class 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Carbon And Carbon Compounds (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999MI000474A IT1309601B1 (it) | 1999-03-09 | 1999-03-09 | Processo per la preparazione di 1,4,7,10 tetraazaciclododecano. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200107380B true ZA200107380B (en) | 2002-09-18 |
Family
ID=11382202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200107380A ZA200107380B (en) | 1999-03-09 | 2001-09-06 | A process for the preparation of 1,4,7,10-tetraazacyclododecane. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6653470B1 (es) |
| EP (1) | EP1159272B1 (es) |
| JP (1) | JP4564667B2 (es) |
| KR (1) | KR100614535B1 (es) |
| CN (1) | CN1155584C (es) |
| AT (1) | ATE277914T1 (es) |
| AU (1) | AU772706B2 (es) |
| CA (1) | CA2366600C (es) |
| DE (1) | DE60014330T2 (es) |
| EA (1) | EA003706B1 (es) |
| ES (1) | ES2228474T3 (es) |
| HK (1) | HK1044770B (es) |
| HU (1) | HU229217B1 (es) |
| IL (2) | IL145298A0 (es) |
| IS (1) | IS2430B (es) |
| IT (1) | IT1309601B1 (es) |
| WO (1) | WO2000053588A1 (es) |
| ZA (1) | ZA200107380B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2830253B1 (fr) * | 2001-09-28 | 2005-02-04 | Air Liquide | Nouveau procede de preparation de macrocycles azotes c-fonctionnalises et nouveaux intermediaires obtenus |
| US11473032B2 (en) | 2010-02-02 | 2022-10-18 | Fuchs Petrolub Se | Constant velocity joint having a boot |
| CN103360333B (zh) * | 2013-07-22 | 2016-03-30 | 厦门市华兴化工有限公司 | 一种高纯度轮环藤宁的制备方法 |
| CN104387336B (zh) * | 2014-10-24 | 2016-04-27 | 上海应用技术学院 | 1,4,7,10-四氮杂环十二烷及其纳滤膜的制备方法 |
| EP4067348A1 (en) | 2021-03-30 | 2022-10-05 | Bracco Imaging SPA | Process for the preparation of cyclen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9504922D0 (en) * | 1995-03-10 | 1995-04-26 | Nycomed As | Process |
| IT1284046B1 (it) * | 1996-06-21 | 1998-05-08 | Bracco Spa | Processo per la preparazione di tetraazamacrocicli |
| IT1291673B1 (it) * | 1997-04-28 | 1999-01-19 | Bracco Spa | Processo per la preparazione di 1,4,7,10 - tetraazaciclododecano |
-
1999
- 1999-03-09 IT IT1999MI000474A patent/IT1309601B1/it active
-
2000
- 2000-03-06 EP EP00910769A patent/EP1159272B1/en not_active Expired - Lifetime
- 2000-03-06 JP JP2000604027A patent/JP4564667B2/ja not_active Expired - Lifetime
- 2000-03-06 CN CNB008047170A patent/CN1155584C/zh not_active Expired - Lifetime
- 2000-03-06 AU AU32860/00A patent/AU772706B2/en not_active Expired
- 2000-03-06 IL IL14529800A patent/IL145298A0/xx active IP Right Grant
- 2000-03-06 AT AT00910769T patent/ATE277914T1/de not_active IP Right Cessation
- 2000-03-06 HU HU0200187A patent/HU229217B1/hu unknown
- 2000-03-06 ES ES00910769T patent/ES2228474T3/es not_active Expired - Lifetime
- 2000-03-06 DE DE60014330T patent/DE60014330T2/de not_active Expired - Lifetime
- 2000-03-06 US US09/914,876 patent/US6653470B1/en not_active Expired - Lifetime
- 2000-03-06 EA EA200100864A patent/EA003706B1/ru not_active IP Right Cessation
- 2000-03-06 KR KR1020017011287A patent/KR100614535B1/ko active IP Right Grant
- 2000-03-06 CA CA002366600A patent/CA2366600C/en not_active Expired - Lifetime
- 2000-03-06 WO PCT/EP2000/001867 patent/WO2000053588A1/en active IP Right Grant
-
2001
- 2001-08-21 IS IS6058A patent/IS2430B/is unknown
- 2001-09-06 ZA ZA200107380A patent/ZA200107380B/en unknown
- 2001-09-06 IL IL145298A patent/IL145298A/en not_active IP Right Cessation
-
2002
- 2002-08-29 HK HK02106376.9A patent/HK1044770B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI990474A1 (it) | 2000-09-09 |
| IL145298A0 (en) | 2002-06-30 |
| JP2002539117A (ja) | 2002-11-19 |
| AU772706B2 (en) | 2004-05-06 |
| HK1044770A1 (en) | 2002-11-01 |
| US6653470B1 (en) | 2003-11-25 |
| HU229217B1 (en) | 2013-09-30 |
| DE60014330T2 (de) | 2005-11-17 |
| HUP0200187A2 (hu) | 2002-05-29 |
| EA200100864A1 (ru) | 2002-02-28 |
| KR100614535B1 (ko) | 2006-08-23 |
| CA2366600A1 (en) | 2000-09-14 |
| EA003706B1 (ru) | 2003-08-28 |
| CN1343203A (zh) | 2002-04-03 |
| HUP0200187A3 (en) | 2003-08-28 |
| KR20020004957A (ko) | 2002-01-16 |
| ATE277914T1 (de) | 2004-10-15 |
| HK1044770B (zh) | 2005-04-01 |
| EP1159272A1 (en) | 2001-12-05 |
| IL145298A (en) | 2006-04-10 |
| EP1159272B1 (en) | 2004-09-29 |
| IS6058A (is) | 2001-08-21 |
| DE60014330D1 (de) | 2004-11-04 |
| AU3286000A (en) | 2000-09-28 |
| CA2366600C (en) | 2009-09-15 |
| CN1155584C (zh) | 2004-06-30 |
| WO2000053588A1 (en) | 2000-09-14 |
| ES2228474T3 (es) | 2005-04-16 |
| IT1309601B1 (it) | 2002-01-24 |
| JP4564667B2 (ja) | 2010-10-20 |
| IS2430B (is) | 2008-10-15 |
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