Ethylenediamine → HCID 21396682, compound

HRID 1439773Notes

Reaction equation

HRID 1439773 reaction equation
[NH2:1][CH2:2][CH2:3][NH2:4].[CH:5]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](=O)[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]2)[CH2:10][CH2:9]1)([CH3:7])[CH3:6].[C:29](#[N:32])[CH:30]=[CH2:31]>>[CH:5]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]([NH:1][CH2:2][CH2:3][NH:4][CH2:31][CH2:30][CH2:29][NH2:32])[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]2)[CH2:10][CH2:9]1)([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 7855AcrylonitrileHCID 213966471,5-Bis[4-(propan-2-yl)cyclohexyl]pentan-3-one

Product 1

HCID 21396682HCID 21396682, compound

Procedure

As an alternative to 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-(4-isopropylcyclohexyl)-3-pentanone, catalytically reduced, then the ring nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish [1,5-di-(4-isopropylcyclohexyl)-3-pentyl]-1,4,8-triazaoctane.

Workup

  1. customAs an alternative to obtaining
  2. customthe reaction

Sources & evidence

ORD record
ord-3a0d87aa058449b180688ab48e252a21
Source dataset
uspto-grants-1977_11
Patent number
US04060639

Reaction notes

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