Ethylenediamine → 1-[1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,4,8-triazaoctane

HRID 1439307

Reaktionsgleichung

Reaktionsgleichung von HRID 1439307
[NH2:1][CH2:2][CH2:3][NH2:4].[CH3:5][C:6]1([CH3:28])[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[CH:7]1[CH2:13][CH2:14][C:15](=O)[CH2:16][CH2:17][CH:18]1[C:23]([CH3:25])([CH3:24])[CH:22]2[CH2:26][CH:19]1[CH2:20][CH2:21]2.N[N].[C:31](#[N:34])[CH:32]=[CH2:33]>>[CH3:5][C:6]1([CH3:28])[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[CH:7]1[CH2:13][CH2:14][CH:15]([NH:1][CH2:2][CH2:3][NH:4][CH2:33][CH2:32][CH2:31][NH2:34])[CH2:16][CH2:17][CH:18]1[C:23]([CH3:25])([CH3:24])[CH:22]2[CH2:26][CH:19]1[CH2:20][CH2:21]2

Komponenten

5

Edukt 4

HCID 3301EthylenediamineHCID 7855AcrylonitrileHCID 213328461,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanoneHCID 178514251Diazen-2-ium-1-ide

Produkt 1

HCID 203273321-[1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,4,8-triazaoctane

Versuchsvorschrift

As an alternative to using an unsymmetrical amine V and obtaining a mixture of Schiff bases VI and VI(a) or VI(b), the reaction can be conducted stepwise. For example, 1,2-diaminoethane may be converted to a Schiff base with 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanone, catalytically reduced, then the remaining primary amino nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-[1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,4,8-triazaoctane.

Aufarbeitung

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Quellen und Nachweise

ORD-Eintrag
ord-9c664da71ee3479290f44c12cac5e318
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04058625

Verknüpfte Notizen

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