N,N'-Bis(2-aminoethyl)-1,3-propanediamine → HCID 9830525, compound

HRID 1941254Notes

Reaction equation

HRID 1941254 reaction equation
[C:1]12[C:18](=[O:19])[O:17][C:15](=O)[C:13]3=[C:14]1[C:5](=[CH:6][C:7]1[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:4]=[CH:3][CH:2]=2.[NH2:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][NH2:30]>C1(C)C=CC=CC=1>[O:17]=[C:15]1[C:13]2[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][C:1]=3[C:18](=[O:19])[N:30]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][N:20]1[C:18](=[O:19])[C:1]3[CH:2]=[CH:3][CH:4]=[C:5]4[C:14]=3[C:13](=[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]3=[CH:6]4)[C:15]1=[O:17])[CH:6]=[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]1=2

Participants

4

Reactant 2

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

Product 1

HCID 9830525HCID 9830525, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1.6 g (6 mmol) of anthracene-1,9-dicarboxylic anhydride in 40 ml of toluene was treated with 0.5 g (3 mmol) of N,N'-bis(2-aminoethyl)-1,3-propanediamine dissolved in 10 ml of toluene. The mixture was refluxed for 4 h and then filtered. The solution was allowed to cool and the solid formed was filtered, washed, dried and recrystallized from toluene. 0.93 g (50%) of N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-1,3-propanediamine were obtained. M.p. 191° C. (toluene). 1 H-NMR (CDCl3) δ=1.84 (q, 2H, J=6 Hz, --CH2 --); 2.74 (broad, s, 2H, NH); 2.89 (t, 4H, J=6 Hz, CH2); 3.02 (t, 4H, J=6 Hz, CH2); 4.31 (t,4H, J=6 Hz, CH2); 7.54 (m, 4H, H-5 and H-9); 7.73 (m, 2H,H-10); 7.89 (d, 2H, J=8 Hz, H-8); 8.22 (d, 1H, J=8 Hz, H-4); 8.51 (s,2H, H-7); 8.57 (d, 2H, J=8 Hz, H-6); 9.78 (d,2H, J=8 Hz, H-11) p.p.m.. Anal. Calculated for C39H32N4O4 : C 75.46; H 5.19; N 9.02. Found: C 75.14; H 5.37; N 8.78. Acetate m.p. 155° C. Methanesulfonate m.p. 243° C.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. filtrationfiltered
  3. temperatureto cool
  4. customthe solid formed
  5. filtrationwas filtered
  6. washwashed
  7. customdried
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3fa892d3c29a46fc9cea43614e5bb919
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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