WO2003095416A1 - Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides - Google Patents
Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides Download PDFInfo
- Publication number
- WO2003095416A1 WO2003095416A1 PCT/EP2002/005021 EP0205021W WO03095416A1 WO 2003095416 A1 WO2003095416 A1 WO 2003095416A1 EP 0205021 W EP0205021 W EP 0205021W WO 03095416 A1 WO03095416 A1 WO 03095416A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acetamide
- alkoxyphenoxyethanamines
- ethyl
- substituted phenol
- alkyloxazoline
- Prior art date
Links
- 0 *C(NCCOc(cccc1)c1O*)=O Chemical compound *C(NCCOc(cccc1)c1O*)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/08—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
Definitions
- the present invention relates to a method for preparing 2- Alkoxyphenoxyethanamines and more particularly relates to the preparation of 2-Alkoxyphenoxyethylacetamides to be used in the method for preparing 2-Alkoxyphenoxyethanamines.
- 2-Alkoxyphenoxyethanamines are known compounds. They are used among others as starting material for the synthesis of pharmaceutical active substances like for example Carvedilol as described in US 4,503,067 and Tamsulosin as described in US 4,731 ,478.
- CH 383 998 discloses a synthesis of 2-Alkoxyphenoxyethanamines in which liquid ammonia is reacted with 2-Methoxyphenoxyethylbromide in methanol. The mixture is heated for ten hours in an autoclave. This method often leads to di- and tri-substituted amines as side products. Unsatisfying yields, complicated isolation procedure and the use of liquid ammonia makes this process very costly.
- the object of the present invention is therefore to provide a process for the.., industrial production of 2-Alkoxyphenoxyethanamines which is cheap and easy to operate.
- the present invention provides the new chemical entity 2-Alkoxyphenoxyethylacetamide as the only intermediate in the process for producing a 2-Alkoxyphenoxyethanamine.
- 2- Alkoxyphenoxyethylacetamide as an easily available intermediate, the number of process steps is reduced with advantage and the raw material employed is easy to obtain and to handle.
- the 2-Alkoxyphenoxyethylacetamide has to be produced by a process, using the reaction of an ortho substituted phenol with a 2-Alkyloxazoline. This reaction only comprises the use of cheap, harmless and easily available raw materials and makes the process for producing 2- Alkoxyphenoxyethanamine suitable for production in industrial scale.
- R ' is selected from the group consisting of methyl or ethyl.
- Alkoxyphenoxyethylacetamide which is a new chemical entity.
- the acetamide can be easily isolated by pouring the reaction mixture into water and collecting the solid residue.
- the acetamide has the formular
- R and R ' are each selected from the group consisting of methyl or ethyl.
- the second step comprises hydrolyzation of the acetamide with water and is obtained in the presence of organic or mineralic acids such as hydrochloric acid or sulfuric acid to give a 2-Alkoxyphenoxyethanamine.
- organic or mineralic acids such as hydrochloric acid or sulfuric acid
- cleavage at the ether oxygen or aromatic ring substitution does not appear, if hydrolysis of the acetamide is performed in the presence of hydrochloric acid.
- the use of phosphoric acid would lead to process water containing phosphate salts. For reasons of environmental protection, these phosphate salts have to be removed from the process water, which again causes costs.
- the reactions may be conducted under atmospheric pressure. Another advantage of the present invention is the absence of a catalyst, as was necessary in one of the methods described in the state of the art.
- the present invention comprises the new chemical entity 2- Methoxyphenoxyethylacetamide, in particular as intermediate compound in the process for production of 2-Alkoxyphenoxyethanamine. It also comprises the use of an ortho substituted phenol for the reaction with an 2-Alkyloxazoline to give the acetamide. It further comprises the use of the 2-Alkyloxazoline for the reaction with the ortho substituted phenol to give the acetamide intermediate and the use of the acetamide intermediate in a hydrolysis reaction to give a 2-Alkoxyphenoxyethanamine.
- Example 2 The procedure of Example 2 is followed except that 223 g of N-[2-(2- Ethoxy-phenoxy)-ethyl]-acetamide are employed. About 126 g of 2-(2- Ethoxy-phenoxy)-ethylamine (70%) are obtained. The 2-(2-Ethoxy- phenoxy)-ethylamine has a boiling point of 94-96°C at 1 Torr.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2002/005021 WO2003095416A1 (en) | 2002-05-07 | 2002-05-07 | Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides |
EP02750895A EP1506156A1 (en) | 2002-05-07 | 2002-05-07 | Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides |
AU2002367923A AU2002367923A1 (en) | 2002-05-07 | 2002-05-07 | Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2002/005021 WO2003095416A1 (en) | 2002-05-07 | 2002-05-07 | Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003095416A1 true WO2003095416A1 (en) | 2003-11-20 |
Family
ID=29414643
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/005021 WO2003095416A1 (en) | 2002-05-07 | 2002-05-07 | Method for preparing 2-alkoxyphenoxyethanamines from 2-alkoxyphenoxyethylacetamides |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1506156A1 (en) |
AU (1) | AU2002367923A1 (en) |
WO (1) | WO2003095416A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017127637A1 (en) | 2016-01-22 | 2017-07-27 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of olefin copolymer dispersant-type viscosity improver and amine compound |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH378343A (en) * | 1959-08-05 | 1964-06-15 | Ciba Geigy | Process for the preparation of new secondary amines |
CH383998A (en) * | 1959-08-05 | 1964-11-15 | Ciba Geigy | Process for the preparation of new secondary amines |
US3412154A (en) * | 1964-08-12 | 1968-11-19 | Parke Davis & Co | Amino-substituted phenone compounds |
US3474134A (en) * | 1960-03-03 | 1969-10-21 | Burroughs Wellcome Co | Phenoxyethyl-guanidines and the salts thereof |
-
2002
- 2002-05-07 EP EP02750895A patent/EP1506156A1/en not_active Withdrawn
- 2002-05-07 AU AU2002367923A patent/AU2002367923A1/en not_active Abandoned
- 2002-05-07 WO PCT/EP2002/005021 patent/WO2003095416A1/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH378343A (en) * | 1959-08-05 | 1964-06-15 | Ciba Geigy | Process for the preparation of new secondary amines |
CH383998A (en) * | 1959-08-05 | 1964-11-15 | Ciba Geigy | Process for the preparation of new secondary amines |
US3474134A (en) * | 1960-03-03 | 1969-10-21 | Burroughs Wellcome Co | Phenoxyethyl-guanidines and the salts thereof |
US3412154A (en) * | 1964-08-12 | 1968-11-19 | Parke Davis & Co | Amino-substituted phenone compounds |
Non-Patent Citations (2)
Title |
---|
FAZIO M J: "Nucleophilic Ring Opening od 2-Oxazolines with Amines: A Convenient Synthesis for Unsymmetrically Substituted Ethylenediamines", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 49, 1984, pages 4889 - 4893, XP002163039, ISSN: 0022-3263 * |
LIS R ET AL: "JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 33, no. 10, 1990, pages 2883 - 2891, XP002089081, ISSN: 0022-2623 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017127637A1 (en) | 2016-01-22 | 2017-07-27 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of olefin copolymer dispersant-type viscosity improver and amine compound |
Also Published As
Publication number | Publication date |
---|---|
EP1506156A1 (en) | 2005-02-16 |
AU2002367923A1 (en) | 2003-11-11 |
AU2002367923A8 (en) | 2003-11-11 |
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