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Process for the preparation of enamines or imines

Assignee: Takasago International Corp
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Filing: 1982-06-30
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Granted: 1987-09-22
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Expires: 2002-06-30
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Abstract

Abstract A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV): [Rh(olefin)L].sup.+ X.sup.- (IV) to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.

Inventors

  • 👤 Seinosuke Otsuka
  • 👤 Kazuhide Tani
  • 👤 Tsuneaki Yamagata
  • 👤 Susumu Akutagawa
  • 👤 Hidenori Kumobayashi
  • 👤 Misao Yagi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 19:18
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/023; C07C; C07C209/00; C07C209/68; C07C45/00; C07C45/51; C07C45/516; C07C45/56

Claims Analysis

Total Claims: 2
Claim 1
Independent Claim 296 words
A process for preparing an enamine represented by formula (II): ##STR57## wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, an alkyl group containing from 1 to 12 carbon atoms, an alkenyl group containing up to 12 carbon atoms, or a phenyl group, wherein R 1 may be substituted by one hydroxy group; R 5 is hydrogen, an alkyl group containing from 1 to 8 carbon atoms, or a cycloalkyl group containing from 6 to 8 carbon atoms; R 6 is an alkyl group containing from 1 to 8 carbon atoms or a cycloalkyl group containing from 6 to 8 carbon atoms; or R 5 and R 6 may combine together in combination with the adjacent nitrogen atom to form pyrrolidine, piperidine or morpholine; or an imine represented by formula (III): ##STR58## wherein R 1 , R 2 , R 3 , R 4 and R 6 are the same as for formula (II), isomerizing an allylamine derivative represented by formula (I): ##STR59## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as for formula (II), using as a catalyst a rhodium complex represented by formula (IV): [Rh(olefin)L].sup.+ X.sup.- wherein olefin represents ethylene, 1,3-butadiene, norbornadiene or cycloocta-1,5-diene; X represents ClO 4 , BF 4 or PF 6 ; and L represents two triarylphosphines wherein the aryl moiety is a phenyl, a tolyl or a naphthyl group or a tri-valent phosphorous compound derivative represented by formula (V): (aryl).sub.2 --P--Y--P--(aryl).sub.2 (V) wherein the aryl moiety is a phenyl, an ortho-tolyl or a metal-tolyl group, or (aryl) 2 is a 2,2'-biphenyl group and Y represents -(CH 2 ) 3 --, --(CH 2 ) 4 --, --(CH 2 ) 5 --, ##STR60##
Claim 2
Dependent Claim 296 words
A process for preparing an enamine represented by formula (II): ##STR57## wherein R 1 , R 2 , R 3 and R 4 are each hydrogen, an alkyl group containing from 1 to 12 carbon atoms, an alkenyl group containing up to 12 carbon atoms, or a phenyl group, wherein R 1 may be substituted by one hydroxy group; R 5 is hydrogen, an alkyl group containing from 1 to 8 carbon atoms, or a cycloalkyl group containing from 6 to 8 carbon atoms; R 6 is an alkyl group containing from 1 to 8 carbon atoms or a cycloalkyl group containing from 6 to 8 carbon atoms; or R 5 and R 6 may combine together in combination with the adjacent nitrogen atom to form pyrrolidine, piperidine or morpholine; or an imine represented by formula (III): ##STR58## wherein R 1 , R 2 , R 3 , R 4 and R 6 are the same as for formula (II), isomerizing an allylamine derivative represented by formula (I): ##STR59## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as for formula (II), using as a catalyst a rhodium complex represented by formula (IV): [Rh(olefin)L].sup.+ X.sup.- wherein olefin represents ethylene, 1,3-butadiene, norbornadiene or cycloocta-1,5-diene; X represents ClO 4 , BF 4 or PF 6 ; and L represents two triarylphosphines wherein the aryl moiety is a phenyl, a tolyl or a naphthyl group or a tri-valent phosphorous compound derivative represented by formula (V): (aryl).sub.2 --P--Y--P--(aryl).sub.2 (V) wherein the aryl moiety is a phenyl, an ortho-tolyl or a metal-tolyl group, or (aryl) 2 is a 2,2'-biphenyl group and Y represents -(CH 2 ) 3 --, --(CH 2 ) 4 --, --(CH 2 ) 5 --, ##STR60##

References Cited (Backward Citations)

US4137417A Cited
US4234484A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-09-21 1991-03-23 1991-09-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-09-21 1995-03-23 1995-09-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-09-21 1999-03-23 1999-09-22 $7700.00 Window Closed / Lapsed

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