N,N'-Bis(2-aminoethyl)-1,3-propanediamine → HCID 21460417, compound

HRID 1941261Notes

Reaction equation

HRID 1941261 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][NH2:11].[C:12]12[C:29](=O)[O:28][C:26](=[O:27])[C:24]3=[C:25]1[C:16](=[CH:17][C:18]1[C:23]3=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:15]=[CH:14][CH:13]=2>C(O)C>[O:27]=[C:26]1[C:24]2[C:25]3[C:16](=[CH:15][CH:14]=[CH:13][C:12]=3[C:29](=[O:28])[N:11]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2][NH2:1])[CH:17]=[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:23]1=2

Participants

4

Reactant 2

HCID 78479N,N'-Bis(2-aminoethyl)-1,3-propanediamineHCID 13155836HCID 13155836, compound

Product 1

HCID 21460417HCID 21460417, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5.0 g (31 mmol) of N,N'-bis(2-aminoethyl)-1,3-propanediamine in 200 ml of ethanol 99% is treated with 1,5 g (6 mmol) of anthracene-1,9-dicarboxylic acid anhydride in 100 ml of ethanol and stirred for 24 hours at room temperature. The solid is collected on a filter, washed with ethanol and crystallized from ethanol to give 0.5 g (20%) of N-[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-N'-(2-aminoethyl)-1,3-propanediamine. M.p. 150° C.

Workup

  1. customThe solid is collected on a filter
  2. washwashed with ethanol
  3. customcrystallized from ethanol

Sources & evidence

ORD record
ord-5556df6b58204cf98f83b8c926e1d279
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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