Preparation of unsaturated amines

Details Preparation of unsaturated amines Preparation of unsaturated amines

C - Chemistry, Metallurgy

07

C

C07C 211/01 (2006.01) C07C 209/26 (2006.01) C07C 209/52 (2006.01) C07C 209/60 (2006.01) C07C 209/68 (2006.01) C07C 209/70 (2006.01) C07C 211/35 (2006.01) C07C 213/08 (2006.01) C07C 215/14 (2006.01) C07C 217/08 (2006.01) C07C 251/04 (2006.01) C07D 213/38 (2006.01) C07D 233/64 (2006.01) C07D 295/03 (2006.01) C07D 295/13 (2006.01) C07D 413/06 (2006.01)

Patent

CA 2105100

Abstract of the disclosure: a process for preparing unsaturated amines of the general formula I Image (I), where R1,R2,R3,R4,R5 are hydrogen, C1- to C20-alkyl, C2- to C20-a1kenY1, C3- to C8-cycloalkyl, C3- to C8-cycloalkenyl, phe~nyl, C7- to C20-phenyl- alkyl, C1- to C20-alkoxy, phenoxy, C7- to C20-phenoxyalkyl, C1- to C20-alkylamino, phenylamino, C7- to C20-phenylalkylamino, pyridyl or imidazolyl, or R1 and R2 or R1 and R3 or R2 and R3 together are a C2- to C8-alkylene which is unsubtituted or monosubstituted to pentasubstituted by C1- to C4-alkyl or unsubstituted or monosub- stituted to tetrasubstituted by amino, N-C1- to C8-alkylamino, N,N-C1- to C8-di- alkylamino, hydroxyl, O-C1- to C8-alkyl- amino and/or C1- to C8-alkoxycarbonyl, and X is =C-N(R4R5) or -C=N-R4, by reacting 2-alkenals of the general formula II Image (II), where R1, R2 and R3 have the abovementioned meanings, with primary or secondary amines of the general formula III - 2 - Image ( III ), where R4 and R5 have the abovementioned meanings, at from (-20) to 70°C and pressures from 0.01 to 100 bar, by carrying out the reaction without removing the water of reaction and transaminating the product to give the compounds I' and hydrogenating the latter to give novel 1,3-diamines of the general formula IV (IV), Image where R1,R2,R3,R4,R5,R6,R7 are hydrogen, C1- to C20-alkyl, C2- to C20-alkenyl, C3- to C8-cycloalkyl, C3- to C8-cycloalkenyl, phenyl, C7- to C20-phenylalkyl, C1- to C20-alkoxy, phenoxy, C7- to C20-phenoxyalkyl, C1- to C20-alkylamino, phenylamino, C7- to C20-phenylalkylamino, pyridyl or imidazolyl, or R1 and R2 or R1 and R3 or R2 and R3 together are a C2- to C8-alkylene which is unsubtituted or monosubstituted to pentasubstituted by C1- to C4-alkyl or unsubstituted or monosubstituted to tetrasubstituted by amino, N-C1- to C8-alkylamino, N,N-C1- to C8-dialkylamino, hydroxyl, O-C1- to C8-alkylamino and/or C1- to C8-alkoxycarbonyl, with the proviso that R1 and R2 are not hydrogen if R3 is methyl and R4 and R5, R6 and R7 are in each case hydrogen or methyl, R4 and R6 are hydrogen and R5 and R7 are ethyl and also R4 and R5, R6 and R7 are in each case together (CH2)5 or (CH2)2-O-(CH2)2, is disclosed.

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