NO327534B1 - Fremgangsmate for fremstilling av salter av cyanobenzylamin - Google Patents
Fremgangsmate for fremstilling av salter av cyanobenzylamin Download PDFInfo
- Publication number
- NO327534B1 NO327534B1 NO20013453A NO20013453A NO327534B1 NO 327534 B1 NO327534 B1 NO 327534B1 NO 20013453 A NO20013453 A NO 20013453A NO 20013453 A NO20013453 A NO 20013453A NO 327534 B1 NO327534 B1 NO 327534B1
- Authority
- NO
- Norway
- Prior art keywords
- cyanobenzylamine
- acid
- hydrochloride
- mass
- hydrogen chloride
- Prior art date
Links
- QIRSDXBXWUTMRE-UHFFFAOYSA-N benzylcyanamide Chemical class N#CNCC1=CC=CC=C1 QIRSDXBXWUTMRE-UHFFFAOYSA-N 0.000 title claims description 56
- 238000000034 method Methods 0.000 title claims description 35
- 150000003839 salts Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 22
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000356 contaminant Substances 0.000 claims description 3
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 description 34
- QREZLLYPLRPULF-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile;hydron;chloride Chemical compound Cl.NCC1=CC=C(C#N)C=C1 QREZLLYPLRPULF-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- QWCORFPFJWNFAN-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile;hydrate Chemical compound O.NCC1=CC=C(C#N)C=C1 QWCORFPFJWNFAN-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- QTHVSMHBQNDAIS-UHFFFAOYSA-N benzylcyanamide;hydrochloride Chemical class Cl.N#CNCC1=CC=CC=C1 QTHVSMHBQNDAIS-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XFKPORAVEUOIRF-UHFFFAOYSA-N 3-(aminomethyl)benzonitrile Chemical compound NCC1=CC=CC(C#N)=C1 XFKPORAVEUOIRF-UHFFFAOYSA-N 0.000 description 3
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001159 Fisher's combined probability test Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005571 anion exchange chromatography Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- -1 α-phthalimido-p-tolyl Chemical group 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- IQKCOMKWSLYAHJ-UHFFFAOYSA-N 2-(aminomethyl)benzonitrile Chemical compound NCC1=CC=CC=C1C#N IQKCOMKWSLYAHJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CEOWWHKHEASODL-UHFFFAOYSA-N 3-(aminomethyl)benzonitrile;hydrate Chemical compound O.NCC1=CC=CC(C#N)=C1 CEOWWHKHEASODL-UHFFFAOYSA-N 0.000 description 1
- VORDNGFQVIFSBE-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)butanenitrile Chemical compound C1=CC=C2C(=O)N(CCCC#N)C(=O)C2=C1 VORDNGFQVIFSBE-UHFFFAOYSA-N 0.000 description 1
- SZCSAPNAYCKVPE-UHFFFAOYSA-N 4-(aminomethyl)-3-chlorobenzonitrile Chemical compound NCC1=CC=C(C#N)C=C1Cl SZCSAPNAYCKVPE-UHFFFAOYSA-N 0.000 description 1
- PAKQBGKIYWXTMG-UHFFFAOYSA-N 4-[(1,3-dioxoisoindol-2-yl)methyl]benzonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=C(C#N)C=C1 PAKQBGKIYWXTMG-UHFFFAOYSA-N 0.000 description 1
- BPGZMPVIXFJEDB-UHFFFAOYSA-N 4-aminobutanenitrile;hydrochloride Chemical compound Cl.NCCCC#N BPGZMPVIXFJEDB-UHFFFAOYSA-N 0.000 description 1
- CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
- WYFWNCCQDVEPIB-UHFFFAOYSA-N ClC=1C(=C(C(NC#N)(Cl)Cl)C=CC=1)Cl Chemical compound ClC=1C(=C(C(NC#N)(Cl)Cl)C=CC=1)Cl WYFWNCCQDVEPIB-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- MYRQANFAWLNKBR-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine;hydrochloride Chemical compound Cl.NCC1=CC=C(CN)C=C1 MYRQANFAWLNKBR-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- IKOZALXAYAQPCS-UHFFFAOYSA-N benzylcyanamide hydrate Chemical class O.N#CNCC1=CC=CC=C1 IKOZALXAYAQPCS-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CXYRUNPLKGGUJF-RAFJPFSSSA-M scopolamine methobromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-RAFJPFSSSA-M 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007858 starting material Substances 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35386299 | 1999-12-14 | ||
| PCT/JP2000/008874 WO2001044171A1 (fr) | 1999-12-14 | 2000-12-14 | Procede de production d'un sel de cyanobenzylamine ou de l'un de ses derives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013453D0 NO20013453D0 (no) | 2001-07-12 |
| NO20013453L NO20013453L (no) | 2001-09-04 |
| NO327534B1 true NO327534B1 (no) | 2009-08-03 |
Family
ID=18433736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013453A NO327534B1 (no) | 1999-12-14 | 2001-07-12 | Fremgangsmate for fremstilling av salter av cyanobenzylamin |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6392083B2 (ru) |
| EP (1) | EP1151989A4 (ru) |
| KR (1) | KR100806326B1 (ru) |
| CN (1) | CN1172905C (ru) |
| AU (1) | AU1890201A (ru) |
| CA (1) | CA2355266C (ru) |
| EA (1) | EA003286B1 (ru) |
| NO (1) | NO327534B1 (ru) |
| WO (1) | WO2001044171A1 (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102503835A (zh) * | 2011-11-14 | 2012-06-20 | 罗梅 | 一种铵盐的合成方法 |
Family Cites Families (10)
| 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 |
| US3515741A (en) * | 1964-04-20 | 1970-06-02 | Boehringer Sohn Ingelheim | 1-cyanophenoxy-2-amino-alkanes |
| DK129447B (da) * | 1967-12-18 | 1974-10-14 | Boehringer Sohn Ingelheim | Analogifremgangsmåde til fremstilling af racemiske eller optisk aktive 1-phenoxy-2-hydroxy-3-sek.-alkylaminopropaner eller syreadditionssalte heraf. |
| US4101671A (en) * | 1973-04-13 | 1978-07-18 | Boehringer Ingelheim Gmbh | Aminobenzyl-amines and salts thereof |
| ZA951617B (en) | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| EP0758341B1 (en) | 1994-04-26 | 2004-03-24 | Aventis Pharmaceuticals, Inc. | FACTOR Xa INHIBITORS |
| JP2937083B2 (ja) | 1995-08-02 | 1999-08-23 | 昭和電工株式会社 | 芳香族シアノメチルアミンの製法 |
| JPH09208546A (ja) * | 1995-11-29 | 1997-08-12 | Ajinomoto Co Inc | 新規置換ベンジルアミンの付加塩及びその光学分割法 |
| SE9802074D0 (sv) * | 1998-06-11 | 1998-06-11 | Astra Ab | New process |
| EP1087770A4 (en) * | 1998-06-15 | 2001-11-14 | Merck & Co Inc | INHIBITORS OF PRENYL PROTEIN TRANSFERASE |
-
2000
- 2000-12-14 AU AU18902/01A patent/AU1890201A/en not_active Abandoned
- 2000-12-14 CA CA002355266A patent/CA2355266C/en not_active Expired - Fee Related
- 2000-12-14 CN CNB008027412A patent/CN1172905C/zh not_active Expired - Fee Related
- 2000-12-14 WO PCT/JP2000/008874 patent/WO2001044171A1/ja active Application Filing
- 2000-12-14 EA EA200100656A patent/EA003286B1/ru not_active IP Right Cessation
- 2000-12-14 EP EP00981730A patent/EP1151989A4/en not_active Withdrawn
- 2000-12-14 KR KR1020017008722A patent/KR100806326B1/ko not_active IP Right Cessation
-
2001
- 2001-06-07 US US09/875,094 patent/US6392083B2/en not_active Expired - Fee Related
- 2001-07-12 NO NO20013453A patent/NO327534B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100806326B1 (ko) | 2008-02-27 |
| CN1172905C (zh) | 2004-10-27 |
| CA2355266A1 (en) | 2001-06-21 |
| NO20013453D0 (no) | 2001-07-12 |
| EA200100656A1 (ru) | 2001-12-24 |
| KR20010101454A (ko) | 2001-11-14 |
| NO20013453L (no) | 2001-09-04 |
| AU1890201A (en) | 2001-06-25 |
| CA2355266C (en) | 2009-11-10 |
| WO2001044171A1 (fr) | 2001-06-21 |
| EP1151989A1 (en) | 2001-11-07 |
| US20010049453A1 (en) | 2001-12-06 |
| EA003286B1 (ru) | 2003-04-24 |
| CN1341096A (zh) | 2002-03-20 |
| EP1151989A4 (en) | 2009-01-21 |
| US6392083B2 (en) | 2002-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |