ES2103681B1 - PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. - Google Patents
PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE.Info
- Publication number
- ES2103681B1 ES2103681B1 ES9501815A ES9501815A ES2103681B1 ES 2103681 B1 ES2103681 B1 ES 2103681B1 ES 9501815 A ES9501815 A ES 9501815A ES 9501815 A ES9501815 A ES 9501815A ES 2103681 B1 ES2103681 B1 ES 2103681B1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- methyl
- propylamine
- product
- 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.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- DVIBDQWVFHDBOP-UHFFFAOYSA-N ethyl 3-hydroxy-3-phenylpropanoate Chemical compound CCOC(=O)CC(O)C1=CC=CC=C1 DVIBDQWVFHDBOP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- XXSDCGNHLFVSET-UHFFFAOYSA-N 3-(methylamino)-1-phenylpropan-1-ol Chemical compound CNCCC(O)C1=CC=CC=C1 XXSDCGNHLFVSET-UHFFFAOYSA-N 0.000 abstract 1
- LIUQUIPHRFFOIE-UHFFFAOYSA-N 3-hydroxy-n-methyl-3-phenylpropanamide Chemical compound CNC(=O)CC(O)C1=CC=CC=C1 LIUQUIPHRFFOIE-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCEDIMIENTO DE PREPARACION DE N-METIL-3-FENIL-3-(P-TRIFLUOROMETILFENOXI)PROPILAMINA. CONSTA DE LAS SIGUIENTES ETAPAS: A) HACER REACCIONAR 3-FENIL-3-HIDROXIPROPIONATO DE ETILO CON METILAMINA PARA DAR N-METIL-3-FENIL-3-HIDROXIPROPANAMIDA; B) REDUCIR ESTE COMPUESTO CON HIDRURO DE LITIO Y ALUMINIO PARA DAR N-METIL-3-FENIL-3-HIDROXIPROPILAMINA; C) HACER REACCIONAR EN DIMETILACETAMIDA, CANTIDADES APROXIMADAMENTE EQUIMOLARES DEL PRODUCTO ANTERIOR, HIDRURO SODICO Y 1-CLORO-4-(TRIFLUOROMETIL)BENCENO, PARA FORMAR EL PRODUCTO DEL TITULO (I); Y D) OPCIONALMENTE, CONVERTIR EL PRODUCTO (I) ASI FORMADO EN SU HIDROCLORURO MEDIANTE LA ADICION DE CLORURO DE HIDROGENO. EL 3-FENIL-3-HIDROXIPROPIONATO DE ETILO DE PARTIDA SE OBTIENE POR CONDENSACION ENTRE BENZALDEHIDO Y ACETATO DE ETILO EN PRESENCIA DE UNA BASE FUERTE, PREFERIBLEMENTE BISTRIMETILSILILAMIDURO DE LITIO. LA INVENCION TIENE UTILIDAD PARA LA PREPARACION INDUSTRIALMENTE VENTAJOSA DE (1).PROCEDURE FOR THE PREPARATION OF N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETHYLPHENOXY) PROPYLAMINE. IT CONSISTS OF THE FOLLOWING STAGES: A) REACT ETHYL 3-PHENYL-3-HYDROXYPROPIONATE WITH METHYLAMINE TO GIVE N-METHYL-3-PHENYL-3-HYDROXYPROPANAMIDE; B) REDUCE THIS COMPOUND WITH LITHIUM AND ALUMINUM HYDRIDE TO GIVE N-METHYL-3-PHENYL-3-HYDROXYPROPYLAMINE; C) REACTION IN DIMETHYLACETAMIDE, QUANTITIES APPROXIMATELY EQUIMOLAR OF THE PREVIOUS PRODUCT, SODIUM HYDRIDE AND 1-CHLORINE-4- (TRIFLUOROMETIL) BENZENE, TO FORM THE PRODUCT OF TITLE (I); AND D) OPTIONALLY, CONVERT THE PRODUCT (I) SO FORMED INTO ITS HYDROCHLORIDE THROUGH THE ADDITION OF HYDROGEN CHLORIDE. STARTING ETHYL 3-PHENYL-3-HYDROXYPROPIONATE IS OBTAINED BY CONDENSATION BETWEEN BENZALDEHYDE AND ETHYL ACETATE IN THE PRESENCE OF A STRONG BASE, PREFERABLY BISTRIMETILSYLILAMIDIDE OF LITHIUM. THE INVENTION IS USEFUL FOR THE INDUSTRIAL ADVANTAGEOUS PREPARATION OF (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501815A ES2103681B1 (en) | 1995-09-19 | 1995-09-19 | PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501815A ES2103681B1 (en) | 1995-09-19 | 1995-09-19 | PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2103681A1 ES2103681A1 (en) | 1997-09-16 |
| ES2103681B1 true ES2103681B1 (en) | 1998-04-01 |
Family
ID=8291611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9501815A Expired - Fee Related ES2103681B1 (en) | 1995-09-19 | 1995-09-19 | PREPARATION PROCEDURE OF N-METHYL-3-PHENYL - (P-TRIFLUOROMETILFENOXI) PROPYLAMINE. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2103681B1 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| ES8707175A1 (en) * | 1986-06-13 | 1987-07-16 | Inke Sa | N-Methyl tri:fluoro:methyl-phenoxy phenyl-propylamine prepn. |
| IT1228209B (en) * | 1989-01-10 | 1991-06-05 | Grato Magnone | PROCEDURE FOR THE PREPARATION OF FLUOXETINE HYDROCHLORIDE. |
| FI81083C (en) * | 1989-03-03 | 1990-09-10 | Orion Yhtymae Oy | ETT FOERBAETTRAT FOERFARANDE FOER FRAMSTAELLNING AV N-METHYL-3- (P-TRIFLUORMETHYLPHENOXY) -3-PHENYLPROPYLAMINE HYDROCHLORIDE. |
| IL99316A (en) * | 1991-08-27 | 1995-03-15 | Teva Pharma | Production of fluoxetine and new intermediates |
| HU9202128D0 (en) * | 1992-06-26 | 1992-10-28 | Richter Gedeon Vegyeszet | Method for producing n-methyl-(3-phenyl-3-(4-[trifluoro-methyl])-phenooxi-)-amine |
-
1995
- 1995-09-19 ES ES9501815A patent/ES2103681B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2103681A1 (en) | 1997-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 19970916 Kind code of ref document: A1 Effective date: 19970916 |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20180806 |