ES2103681A1 - Process for the preparation of N-methyl-3-phenyl-3-(p- trifluoromethylphenoxy)propylamine - Google Patents
Process for the preparation of N-methyl-3-phenyl-3-(p- trifluoromethylphenoxy)propylamineInfo
- Publication number
- ES2103681A1 ES2103681A1 ES09501815A ES9501815A ES2103681A1 ES 2103681 A1 ES2103681 A1 ES 2103681A1 ES 09501815 A ES09501815 A ES 09501815A ES 9501815 A ES9501815 A ES 9501815A ES 2103681 A1 ES2103681 A1 ES 2103681A1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- methyl
- preparation
- trifluoromethylphenoxy
- 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
- 238000002360 preparation method Methods 0.000 title abstract 3
- 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 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 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
- 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
- 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-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
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-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
Process for the preparation of N-methyl-3-phenyl-(p- trifluoromethylphenoxy)propylamine Comprises the following stages: a) reacting the ethyl 3- phenyl-3-hydroxypropionate with methylamine to yield N-methyl-3-phenyl-3-hydroxypropanamide, b) reducing this compound with lithium aluminium hydride to yield N-methyl-3-phenyl-3-hydroxypropylamine, c) reacting approximately equimolar quantities of the above product, sodium hydride and 1-chloro-4-(trifluoromethyl) benzene in dimethylacetamide to form the title product I, and d) optionally converting the product I so formed into its hydrochloride by the addition of hydrogen chloride. The starting ethyl 3-phenyl-3-hydroxypropionate is obtained by condensation between benzaldehyde and ethyl acetate in the presence of a strong base, preferably lithium bistrimethylsilylamide. The invention is of use in the industrially advantageous preparation of I.
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 true ES2103681A1 (en) | 1997-09-16 |
| ES2103681B1 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) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES433720A1 (en) * | 1974-01-10 | 1976-12-01 | Lilly Co Eli | Arloxyphenylpropylamines |
| ES8707175A1 (en) * | 1986-06-13 | 1987-07-16 | Inke Sa | PROCEDURE FOR OBTAINING N-METHYL-3- (P-TRIFLUOROMETILFENOXI) -3-PHENYLPROPYLAMINE |
| EP0529842A2 (en) * | 1991-08-27 | 1993-03-03 | Teva Pharmaceutical Industries, Ltd. | Production of fluoxetine and new intermediates |
| WO1994000416A1 (en) * | 1992-06-26 | 1994-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof |
| ES2057187T3 (en) * | 1989-01-10 | 1994-10-16 | Grato Magnone | PROCEDURE FOR THE PREPARATION OF FLUOXETINE CHLORHYDRATE. |
| ES2062131T3 (en) * | 1989-03-03 | 1994-12-16 | Orion Yhtymae Oy | PROCEDURE FOR THE PREPARATION OF N-METHYL-3- (P-TRIFLUOROMETILFENOXI) -3-PHENYLPROPYLAMINE AND ITS SALTS. |
-
1995
- 1995-09-19 ES ES9501815A patent/ES2103681B1/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES433720A1 (en) * | 1974-01-10 | 1976-12-01 | Lilly Co Eli | Arloxyphenylpropylamines |
| ES8707175A1 (en) * | 1986-06-13 | 1987-07-16 | Inke Sa | PROCEDURE FOR OBTAINING N-METHYL-3- (P-TRIFLUOROMETILFENOXI) -3-PHENYLPROPYLAMINE |
| ES2057187T3 (en) * | 1989-01-10 | 1994-10-16 | Grato Magnone | PROCEDURE FOR THE PREPARATION OF FLUOXETINE CHLORHYDRATE. |
| ES2062131T3 (en) * | 1989-03-03 | 1994-12-16 | Orion Yhtymae Oy | PROCEDURE FOR THE PREPARATION OF N-METHYL-3- (P-TRIFLUOROMETILFENOXI) -3-PHENYLPROPYLAMINE AND ITS SALTS. |
| EP0529842A2 (en) * | 1991-08-27 | 1993-03-03 | Teva Pharmaceutical Industries, Ltd. | Production of fluoxetine and new intermediates |
| WO1994000416A1 (en) * | 1992-06-26 | 1994-01-06 | Richter Gedeon Vegyészeti Gyár Rt. | Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2103681B1 (en) | 1998-04-01 |
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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 |