Ethylenediamine → 1-[1,5-Di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentyl]-1,4,8-triazaoctane

HRID 866708Notes

Reaction equation

HRID 866708 reaction equation
[NH2:1][CH2:2][CH2:3][NH2:4].[CH3:5][CH:6]1[CH:11]2[CH2:12][CH2:13][CH:8]([CH2:9][CH2:10]2)[CH:7]1[CH2:14][CH2:15][C:16](=O)[CH2:17][CH2:18][CH:19]1[CH:24]([CH3:25])[CH:23]2[CH2:26][CH2:27][CH:20]1[CH2:21][CH2:22]2.N[N].[C:31](#[N:34])[CH:32]=[CH2:33]>>[CH3:5][CH:6]1[CH:11]2[CH2:12][CH2:13][CH:8]([CH2:9][CH2:10]2)[CH:7]1[CH2:14][CH2:15][CH:16]([NH:1][CH2:2][CH2:3][NH:4][CH2:33][CH2:32][CH2:31][NH2:34])[CH2:17][CH2:18][CH:19]1[CH:24]([CH3:25])[CH:23]2[CH2:26][CH2:27][CH:20]1[CH2:21][CH2:22]2

Participants

5

Reactant 4

HCID 3301EthylenediamineHCID 7855AcrylonitrileHCID 203198001,5-Di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentanoneHCID 178514251Diazen-2-ium-1-ide

Product 1

HCID 203198271-[1,5-Di-(3-methylbicyclo[2.2.2]oct-2-yl)-3-pentyl]-1,4,8-triazaoctane

Procedure

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-methylbicyclo[2.2.2]oct-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-methylbicyclo[2.2.2]oct-2-yl)-3-pentyl]-1,4,8-triazaoctane.

Workup

  1. customobtaining
  2. customthe reaction

Sources & evidence

ORD record
ord-8b540553200b44daa239b944002c6383
Source dataset
uspto-grants-1978_07
Patent number
US04100193

Reaction notes

Loading…