EP1506156A1 - Procede de preparation de 2-alkoxyphenoxyethanamines a partir de 2-alkoxyphenoxyethylacetamides - Google Patents

Procede de preparation de 2-alkoxyphenoxyethanamines a partir de 2-alkoxyphenoxyethylacetamides

Info

Publication number
EP1506156A1
EP1506156A1 EP02750895A EP02750895A EP1506156A1 EP 1506156 A1 EP1506156 A1 EP 1506156A1 EP 02750895 A EP02750895 A EP 02750895A EP 02750895 A EP02750895 A EP 02750895A EP 1506156 A1 EP1506156 A1 EP 1506156A1
Authority
EP
European Patent Office
Prior art keywords
acetamide
alkoxyphenoxyethanamines
ethyl
substituted phenol
alkyloxazoline
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.)
Withdrawn
Application number
EP02750895A
Other languages
German (de)
English (en)
Inventor
Carsten Materne
Iman Khan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MCM PHARMA GmbH
NAKODA CHEMICALS Ltd
Original Assignee
MCM PHARMA GmbH
NAKODA CHEMICALS Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by MCM PHARMA GmbH, NAKODA CHEMICALS Ltd filed Critical MCM PHARMA GmbH
Publication of EP1506156A1 publication Critical patent/EP1506156A1/fr
Withdrawn legal-status Critical Current

Links

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

La présente invention concerne un procédé de préparation de 2-Alkoxyphénoxyéthanamines, et plus particulièrement, la préparation de nouveaux composés chimiques 2-Alkoxyphénoxyethylacétamides, en particulier, comme produits intermédiaires. L'invention concerne aussi un procédé pour la synthèse de 2-Alkoxyphénoxyéthanamines qui est facile et peu onéreux à mettre en oeuvre, et présente une grande utilité pour ceux versés dansl art. La présente invention a ainsi pour objet un procédé pour la production industrielle de phénoxyéthanamine qui est facile et peu onéreux à mettre enoeuvre. Cet objet est réalisé par le composé 2-Alkoxyphénoxyacétamide qui est préparé en faisant réagir un phénol ortho-substitué avec une 2-Alkyloxazoline. On obtient la 2-Alkylphénoxyéthanamine par hydrolyse de l'acétamide avec de l'eau en présence d'acides organiques ou minéraux comme de l'acide chlorhydrique et/ou de l'acide sulfurique.
EP02750895A 2002-05-07 2002-05-07 Procede de preparation de 2-alkoxyphenoxyethanamines a partir de 2-alkoxyphenoxyethylacetamides Withdrawn EP1506156A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2002/005021 WO2003095416A1 (fr) 2002-05-07 2002-05-07 Procede de preparation de 2-alkoxyphenoxyethanamines a partir de 2-alkoxyphenoxyethylacetamides

Publications (1)

Publication Number Publication Date
EP1506156A1 true EP1506156A1 (fr) 2005-02-16

Family

ID=29414643

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02750895A Withdrawn EP1506156A1 (fr) 2002-05-07 2002-05-07 Procede de preparation de 2-alkoxyphenoxyethanamines a partir de 2-alkoxyphenoxyethylacetamides

Country Status (3)

Country Link
EP (1) EP1506156A1 (fr)
AU (1) AU2002367923A1 (fr)
WO (1) WO2003095416A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3405554B1 (fr) 2016-01-22 2019-12-25 Chevron Oronite Company LLC Composition d'huile lubrifiante contenant en mélange un agent améliorant la viscosité de type dispersant à base de copolymère d'oléfine et un composé d'amine

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH383998A (de) * 1959-08-05 1964-11-15 Ciba Geigy Verfahren zur Herstellung neuer sekundärer Amine
CH378343A (de) * 1959-08-05 1964-06-15 Ciba Geigy Verfahren zur Herstellung neuer sekundärer Amine
US3474134A (en) * 1960-03-03 1969-10-21 Burroughs Wellcome Co Phenoxyethyl-guanidines and the salts thereof
US3261829A (en) * 1964-08-12 1966-07-19 Searle & Co Spiro(steroidal-6,3'-1-pyrazolines) and process

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03095416A1 *

Also Published As

Publication number Publication date
WO2003095416A1 (fr) 2003-11-20
AU2002367923A8 (en) 2003-11-11
AU2002367923A1 (en) 2003-11-11

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