3,3',3'',3'''-(Propane-1,3-diyldinitrilo)tetrapropanenitrile → 1,3-Propanediamine, N,N,N',N'-tetrakis(3-aminopropyl)-

HRID 658321Notes

Reaction equation

HRID 658321 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([CH2:18][CH2:19][C:20]#[N:21])[CH2:6][CH2:7][CH2:8][N:9]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:11][C:12]#[N:13])#[N:2].[H][H]>O1CCOCC1>[NH2:13][CH2:12][CH2:11][CH2:10][N:9]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:8][CH2:7][CH2:6][N:5]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:4][CH2:3][CH2:1][NH2:2]

Participants

4

Reactant 2

HCID 202317073,3',3'',3'''-(Propane-1,3-diyldinitrilo)tetrapropanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 116810301,3-Propanediamine, N,N,N',N'-tetrakis(3-aminopropyl)-Yield 87.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20.05 g of N,N,N′,N′-tetrakis(2-cyanoethyl)-1,3-propanediamine, 2.01 g of Raney Co and 100 mL of 1,4-dioxane were charged in an autoclave and a hydrogenation reaction was carried out at an initial hydrogen pressure of 9.0 MPa at 150° C. for 3 hours. After the catalyst was removed by filtration, the obtained filtrate was concentrated to dryness to give 18.57 g of the title compound as a pale yellow oil.

Workup

  1. customa hydrogenation reaction
  2. customAfter the catalyst was removed by filtration
  3. concentrationthe obtained filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-6a3e9c63f5a6473facb702cea961b363
Source dataset
uspto-grants-2011_12
Patent number
US08076478B2

Reaction notes

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