ES2006418A4 - Nuevo procedimiento para la sintesis del alfa-(1-metil-etil)-3,4-dimetoxi-benceno-aceto-nitrilo. - Google Patents
Nuevo procedimiento para la sintesis del alfa-(1-metil-etil)-3,4-dimetoxi-benceno-aceto-nitrilo.Info
- Publication number
- ES2006418A4 ES2006418A4 ES88104469T ES88104469T ES2006418A4 ES 2006418 A4 ES2006418 A4 ES 2006418A4 ES 88104469 T ES88104469 T ES 88104469T ES 88104469 T ES88104469 T ES 88104469T ES 2006418 A4 ES2006418 A4 ES 2006418A4
- Authority
- ES
- Spain
- Prior art keywords
- nitrile
- dimetoxi
- aceto
- benzene
- ethyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 3
- -1 1-METHYL-ETHYL Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 abstract 1
- 238000003476 Darzens condensation reaction Methods 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 230000021523 carboxylation Effects 0.000 abstract 1
- 238000006473 carboxylation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 1
- 229960001722 verapamil Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Abstract
NUEVO PROCESO PARA LA SINTESIS DEL ALFA-(1-METILETIL)-3,4 -DIMETOXIACETONITRILO DE FORMULA (I) QUE ES UN INTERMEDIARIO EN LA SINTESIS DE LA DROGA INTERNACIONALMENTE CONOCIDO COMO VERAPAMIL.EL PROCESO COMIENZA A PARTIR DEL ISOBUTIRIL-3,4-DIMETOXIBENCENO DE FORMULA (II) LA CUAL, POR MEDIO DE LA CONDENSACION DARZENS, DA UN EXPOSIESTER, EL CUAL POR HIDROLISIS ALCALINA Y SUBSECUENTEMENTE DE CARBOXILACION, DA EL ALFA-(1-METILETIL) -3,4-DIMETOXIBENCENO ACETALDEHIDO.ESTE PRODUCTO SE SOMETE A REACCION CON HIDROXILAMINA PARA OBTENER LA CORRESPONDIENTE OXINA, QUE POR DESHIDRATACION DA EL NITRILO DE FORMULA (I).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8720019A IT1215409B (it) | 1987-04-08 | 1987-04-08 | Processo per la sintesi dell'alfa-(1-metiletil)-3,4-dimetossibenzeneacetonitrile. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2006418A4 true ES2006418A4 (es) | 1989-05-01 |
| ES2006418T3 ES2006418T3 (es) | 1994-07-16 |
Family
ID=11163169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES88104469T Expired - Lifetime ES2006418T3 (es) | 1987-04-08 | 1988-03-21 | Nuevo procedimiento para la sintesis del alfa-(1-metil-etil)-3,4-dimetoxi-benceno-aceto-nitrilo. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5097058A (es) |
| EP (1) | EP0285890B1 (es) |
| JP (1) | JPH0717592B2 (es) |
| KR (1) | KR940011907B1 (es) |
| AR (1) | AR243158A1 (es) |
| AT (1) | ATE82566T1 (es) |
| AU (1) | AU605571B2 (es) |
| CA (1) | CA1327048C (es) |
| DD (1) | DD273250A5 (es) |
| DE (2) | DE3875996T2 (es) |
| DK (1) | DK189088A (es) |
| ES (1) | ES2006418T3 (es) |
| FI (1) | FI93950C (es) |
| GR (2) | GR880300180T1 (es) |
| IE (1) | IE62321B1 (es) |
| IL (1) | IL85836A (es) |
| IT (1) | IT1215409B (es) |
| NO (1) | NO168032C (es) |
| NZ (1) | NZ223966A (es) |
| PL (1) | PL152661B1 (es) |
| PT (1) | PT87187B (es) |
| YU (1) | YU47119B (es) |
| ZA (1) | ZA881961B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1229214B (it) * | 1989-03-31 | 1991-07-25 | Alfa Wassermann S P A Contrada | Processo per la sintesi della n metil 3,4 dimetossifeniletilamina |
| ATE106186T1 (de) * | 1990-12-28 | 1994-06-15 | Unilever Nv | Verbesserter, tiefgefrorener, vorgegärter teig. |
| US5457222A (en) * | 1991-07-25 | 1995-10-10 | Kao Corporation | Process for producing nitrile |
| EP1445248A4 (en) | 2001-11-12 | 2006-03-22 | Kuraray Co | PROCESS FOR THE PREPARATION OF CYCLOPROPYLETHANOL AND CYLCOPROPYLACETONITRILE AND INTERMEDIATE PRODUCTS FOR THE TWO COMPOUNDS |
| JP2010180142A (ja) * | 2009-02-03 | 2010-08-19 | Kuraray Co Ltd | シクロヘキサンカルボニトリルの製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1154810B (de) * | 1961-04-01 | 1963-09-26 | Knoll Ag | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
| US3435075A (en) * | 1965-06-15 | 1969-03-25 | Merck & Co Inc | Process for preparing (halophenyl) alkyl ketone compounds |
| US3415866A (en) * | 1966-03-14 | 1968-12-10 | Colgate Palmolive Co | alpha-alkylidene-3,4-disubstituted-phenylacetonitriles |
| JPS5118940B2 (es) * | 1971-12-25 | 1976-06-14 | ||
| US3997608A (en) * | 1973-07-05 | 1976-12-14 | Richardson-Merrell Inc. | N-substituted-dihydroxyphenethylamines |
| US4235807A (en) * | 1979-07-02 | 1980-11-25 | Thompson-Hayward Chemical Company | Synthesis of 2,6-disubstituted benzonitriles |
| US4456562A (en) * | 1981-12-02 | 1984-06-26 | Sumitomo Chemical Company, Limited | Process for producing nitriles |
| DE3468863D1 (en) * | 1984-06-15 | 1988-02-25 | Heumann Ludwig & Co Gmbh | Method for the preparation of phenylacetonitrile substituted by a basic radical |
| US4593042A (en) * | 1985-10-18 | 1986-06-03 | G. D. Searle & Co. | Bicyclo-substituted phenylacetonitrile derivatives |
-
1987
- 1987-04-08 IT IT8720019A patent/IT1215409B/it active
-
1988
- 1988-03-18 ZA ZA881961A patent/ZA881961B/xx unknown
- 1988-03-21 DE DE8888104469T patent/DE3875996T2/de not_active Expired - Fee Related
- 1988-03-21 AT AT88104469T patent/ATE82566T1/de not_active IP Right Cessation
- 1988-03-21 ES ES88104469T patent/ES2006418T3/es not_active Expired - Lifetime
- 1988-03-21 NZ NZ223966A patent/NZ223966A/xx unknown
- 1988-03-21 EP EP88104469A patent/EP0285890B1/en not_active Expired - Lifetime
- 1988-03-21 DE DE198888104469T patent/DE285890T1/de active Pending
- 1988-03-23 IL IL85836A patent/IL85836A/xx not_active IP Right Cessation
- 1988-04-06 CA CA000563389A patent/CA1327048C/en not_active Expired - Fee Related
- 1988-04-06 KR KR1019880003818A patent/KR940011907B1/ko not_active Expired - Fee Related
- 1988-04-06 PL PL1988271678A patent/PL152661B1/pl unknown
- 1988-04-06 DD DD88314466A patent/DD273250A5/de not_active IP Right Cessation
- 1988-04-07 YU YU69688A patent/YU47119B/sh unknown
- 1988-04-07 IE IE103388A patent/IE62321B1/en not_active IP Right Cessation
- 1988-04-07 FI FI881611A patent/FI93950C/fi not_active IP Right Cessation
- 1988-04-07 AU AU14375/88A patent/AU605571B2/en not_active Ceased
- 1988-04-07 AR AR88310506A patent/AR243158A1/es active
- 1988-04-07 NO NO881487A patent/NO168032C/no not_active IP Right Cessation
- 1988-04-07 DK DK189088A patent/DK189088A/da not_active Application Discontinuation
- 1988-04-07 PT PT87187A patent/PT87187B/pt not_active IP Right Cessation
- 1988-04-08 JP JP63087039A patent/JPH0717592B2/ja not_active Expired - Fee Related
-
1989
- 1989-06-22 GR GR88300180T patent/GR880300180T1/el unknown
-
1990
- 1990-04-25 US US07/512,909 patent/US5097058A/en not_active Expired - Lifetime
-
1992
- 1992-11-30 GR GR920402453T patent/GR3006382T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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