WO2001044162A1 - Procede de preparation d'amines secondaires - Google Patents

Procede de preparation d'amines secondaires Download PDF

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Publication number
WO2001044162A1
WO2001044162A1 PCT/US2000/026581 US0026581W WO0144162A1 WO 2001044162 A1 WO2001044162 A1 WO 2001044162A1 US 0026581 W US0026581 W US 0026581W WO 0144162 A1 WO0144162 A1 WO 0144162A1
Authority
WO
WIPO (PCT)
Prior art keywords
palladium
process according
ferrocene
methyl
ligand
Prior art date
Application number
PCT/US2000/026581
Other languages
English (en)
Inventor
Sue L. Lin
Weixia M. Zhou
George W. Matcham
Original Assignee
Celgro
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
Priority to PCT/US2000/026581 priority Critical patent/WO2001044162A1/fr
Application filed by Celgro filed Critical Celgro
Priority to AU77243/00A priority patent/AU7724300A/en
Priority to HU0203901A priority patent/HUP0203901A3/hu
Priority to KR1020027007564A priority patent/KR20020073140A/ko
Priority to JP2001545251A priority patent/JP2004507443A/ja
Priority to NZ519366A priority patent/NZ519366A/en
Priority to IL14980700A priority patent/IL149807A0/xx
Priority to EP00966976A priority patent/EP1237844A1/fr
Priority to CA002394519A priority patent/CA2394519A1/fr
Priority to MXPA02005810A priority patent/MXPA02005810A/es
Priority to BR0016348-1A priority patent/BR0016348A/pt
Publication of WO2001044162A1 publication Critical patent/WO2001044162A1/fr
Priority to FI20020955A priority patent/FI20020955A/fi

Links

Classifications

    • 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
    • C07C213/02—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 involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Selon l'invention, on prépare des amines N,N-disubstituées dans lesquelles l'atome amino-azote est lié à l'atome de carbone d'un noyau aromatique disubstitué en positions ortho par rapport à l'atome de carbone, en faisant réagir une amine primaire et un composé renfermant un composé aromatique ortho ou ortho-disusbtitué comportant un susbtituant nucléofuge dans un environnement basique et en présence d'un complexe du palladium(0) catalytique et d'un ligand, le rapport complexe du palladium/ligand étant supérieur à 1:1 au moins. Selon un mode de réalisation typique, on fait réagir un 2-méthyl-6-éthylphényl-trifluorométhylsulfonate et un (S)-1-méthoxy-2-aminopropane en présence de bis(dibenzylidèneacétone)palladium, tri-tert.-butylphosphine et de tert.-butoxyde de sodium, de manière à obtenir une (S)-N-(1-méthoxyprop-2-yl)-2-méthyl-6-éthylphénylamine.
PCT/US2000/026581 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires WO2001044162A1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
NZ519366A NZ519366A (en) 1999-12-14 2000-09-27 Process for the preparation of secondary and tertiary amines
AU77243/00A AU7724300A (en) 1999-12-14 2000-09-27 Process for the preparation of secondary and tertiary amines
HU0203901A HUP0203901A3 (en) 1999-12-14 2000-09-27 Process for the preparation of secondary and tertiary amines
KR1020027007564A KR20020073140A (ko) 1999-12-14 2000-09-27 2차 및 3차 아민의 제조방법
JP2001545251A JP2004507443A (ja) 1999-12-14 2000-09-27 第２級及び第３級アミンの調製方法
PCT/US2000/026581 WO2001044162A1 (fr) 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires
IL14980700A IL149807A0 (en) 1999-12-14 2000-09-27 Process for the preparation of secondary and tertiary amines
MXPA02005810A MXPA02005810A (es) 1999-12-14 2000-09-27 Procedimiento para la preparacion de aminas secundarias y terciarias.
CA002394519A CA2394519A1 (fr) 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires
EP00966976A EP1237844A1 (fr) 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires
BR0016348-1A BR0016348A (pt) 1999-12-14 2000-09-27 Processo para a preparação de aminas secundárias e terciárias
FI20020955A FI20020955A (fi) 1999-12-14 2002-05-21 Menetelmä sekundääristen ja tertiääristen amiinien valmistamiseksi

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60/107,521 1999-12-14
PCT/US2000/026581 WO2001044162A1 (fr) 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires

Publications (1)

Publication Number Publication Date
WO2001044162A1 true WO2001044162A1 (fr) 2001-06-21

Family

ID=21741817

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/026581 WO2001044162A1 (fr) 1999-12-14 2000-09-27 Procede de preparation d'amines secondaires

Country Status (1)

Country Link
WO (1) WO2001044162A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4757144A (en) * 1983-12-16 1988-07-12 Kao Corporation Preparing tertiary amine from formaldehyde and primary and/or secondary amine
US4792622A (en) * 1985-12-25 1988-12-20 Kao Corporation Process for preparation of secondary amine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4757144A (en) * 1983-12-16 1988-07-12 Kao Corporation Preparing tertiary amine from formaldehyde and primary and/or secondary amine
US4792622A (en) * 1985-12-25 1988-12-20 Kao Corporation Process for preparation of secondary amine

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