ZA200006607B - New process. - Google Patents
New process. Download PDFInfo
- Publication number
- ZA200006607B ZA200006607B ZA200006607A ZA200006607A ZA200006607B ZA 200006607 B ZA200006607 B ZA 200006607B ZA 200006607 A ZA200006607 A ZA 200006607A ZA 200006607 A ZA200006607 A ZA 200006607A ZA 200006607 B ZA200006607 B ZA 200006607B
- Authority
- ZA
- South Africa
- Prior art keywords
- salt
- alkanesulphonate
- cyanobenzylamine
- salts
- hydrogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 61
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 19
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 10
- QIRSDXBXWUTMRE-UHFFFAOYSA-N benzylcyanamide Chemical class N#CNCC1=CC=CC=C1 QIRSDXBXWUTMRE-UHFFFAOYSA-N 0.000 claims abstract description 9
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims abstract description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229960004592 isopropanol Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical group CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 7
- RNKJJCGSKICAIX-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile;methanesulfonic acid Chemical compound CS(O)(=O)=O.NCC1=CC=C(C#N)C=C1 RNKJJCGSKICAIX-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- -1 Platinum Metals Chemical class 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005897 peptide coupling reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LEEKVSKFSUKMKM-UHFFFAOYSA-N benzene methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.c1ccccc1 LEEKVSKFSUKMKM-UHFFFAOYSA-N 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 201000007750 congenital bile acid synthesis defect Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RIUKRCNLZYDWHS-UHFFFAOYSA-N ethane;methanesulfonic acid Chemical compound CC.CS(O)(=O)=O RIUKRCNLZYDWHS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Separation By Low-Temperature Treatments (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9802074A SE9802074D0 (sv) | 1998-06-11 | 1998-06-11 | New process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006607B true ZA200006607B (en) | 2002-02-14 |
Family
ID=20411659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006607A ZA200006607B (en) | 1998-06-11 | 2000-11-14 | New process. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6284913B1 (ja) |
| EP (1) | EP1086074B1 (ja) |
| JP (1) | JP4330270B2 (ja) |
| KR (1) | KR100625151B1 (ja) |
| CN (1) | CN1181051C (ja) |
| AT (1) | ATE263750T1 (ja) |
| AU (1) | AU748960B2 (ja) |
| BR (1) | BR9911146A (ja) |
| CA (1) | CA2333275C (ja) |
| DE (1) | DE69916269T2 (ja) |
| DK (1) | DK1086074T3 (ja) |
| ES (1) | ES2217771T3 (ja) |
| IL (2) | IL139642A0 (ja) |
| NO (1) | NO20006250L (ja) |
| NZ (1) | NZ508351A (ja) |
| PT (1) | PT1086074E (ja) |
| SE (1) | SE9802074D0 (ja) |
| WO (1) | WO1999064391A1 (ja) |
| ZA (1) | ZA200006607B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5088598B2 (ja) * | 1999-12-14 | 2012-12-05 | 昭和電工株式会社 | シアノベンジルアミン類の塩の製造方法 |
| EA003286B1 (ru) * | 1999-12-14 | 2003-04-24 | Сова Денко К.К. | Способ получения солей цианобензиламинов |
| JP4692700B2 (ja) * | 2001-01-11 | 2011-06-01 | 三菱瓦斯化学株式会社 | 芳香族シアノアミノメチルの製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB814631A (en) | 1957-01-10 | 1959-06-10 | Distillers Co Yeast Ltd | The production of cyano benzylamines |
| US3050544A (en) | 1959-04-30 | 1962-08-21 | Allied Chem | Cyanobenzyl amine |
| DE1643365A1 (de) | 1967-09-29 | 1971-04-22 | Hoechst Ag | Verfahren zur Herstellung von m- und p-Cyanbenzylamin und deren Hexahydroderivaten |
| JPS5124494B2 (ja) | 1972-12-20 | 1976-07-24 | ||
| WO1998033766A1 (fr) * | 1997-02-04 | 1998-08-06 | Showa Denko K.K. | Procede de preparation de cyanoarylmethylamine |
-
1998
- 1998-06-11 SE SE9802074A patent/SE9802074D0/xx unknown
-
1999
- 1999-06-10 US US09/341,981 patent/US6284913B1/en not_active Expired - Fee Related
- 1999-06-10 CA CA002333275A patent/CA2333275C/en not_active Expired - Fee Related
- 1999-06-10 PT PT99930104T patent/PT1086074E/pt unknown
- 1999-06-10 DE DE69916269T patent/DE69916269T2/de not_active Expired - Lifetime
- 1999-06-10 IL IL13964299A patent/IL139642A0/xx unknown
- 1999-06-10 AT AT99930104T patent/ATE263750T1/de not_active IP Right Cessation
- 1999-06-10 NZ NZ508351A patent/NZ508351A/xx unknown
- 1999-06-10 WO PCT/SE1999/001032 patent/WO1999064391A1/en active IP Right Grant
- 1999-06-10 DK DK99930104T patent/DK1086074T3/da active
- 1999-06-10 KR KR1020007013992A patent/KR100625151B1/ko not_active IP Right Cessation
- 1999-06-10 BR BR9911146-2A patent/BR9911146A/pt not_active Application Discontinuation
- 1999-06-10 AU AU46711/99A patent/AU748960B2/en not_active Ceased
- 1999-06-10 CN CNB998072648A patent/CN1181051C/zh not_active Expired - Fee Related
- 1999-06-10 JP JP2000553401A patent/JP4330270B2/ja not_active Expired - Fee Related
- 1999-06-10 EP EP99930104A patent/EP1086074B1/en not_active Expired - Lifetime
- 1999-06-10 ES ES99930104T patent/ES2217771T3/es not_active Expired - Lifetime
-
2000
- 2000-11-13 IL IL139642A patent/IL139642A/en not_active IP Right Cessation
- 2000-11-14 ZA ZA200006607A patent/ZA200006607B/en unknown
- 2000-12-08 NO NO20006250A patent/NO20006250L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL139642A (en) | 2008-07-08 |
| AU748960B2 (en) | 2002-06-13 |
| NZ508351A (en) | 2002-11-26 |
| DK1086074T3 (da) | 2004-07-05 |
| US6284913B1 (en) | 2001-09-04 |
| JP2002517481A (ja) | 2002-06-18 |
| NO20006250L (no) | 2001-02-09 |
| IL139642A0 (en) | 2002-02-10 |
| DE69916269D1 (de) | 2004-05-13 |
| JP4330270B2 (ja) | 2009-09-16 |
| PT1086074E (pt) | 2004-08-31 |
| ES2217771T3 (es) | 2004-11-01 |
| KR20010052720A (ko) | 2001-06-25 |
| EP1086074A1 (en) | 2001-03-28 |
| CA2333275C (en) | 2009-02-03 |
| ATE263750T1 (de) | 2004-04-15 |
| EP1086074B1 (en) | 2004-04-07 |
| CN1181051C (zh) | 2004-12-22 |
| AU4671199A (en) | 1999-12-30 |
| KR100625151B1 (ko) | 2006-09-20 |
| NO20006250D0 (no) | 2000-12-08 |
| SE9802074D0 (sv) | 1998-06-11 |
| CN1305455A (zh) | 2001-07-25 |
| DE69916269T2 (de) | 2005-04-28 |
| CA2333275A1 (en) | 1999-12-16 |
| WO1999064391A1 (en) | 1999-12-16 |
| BR9911146A (pt) | 2001-03-06 |
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