1,3-Propanediamine → HCID 9830525, compound

HRID 1941258Notes

Reaction equation

HRID 1941258 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][N:13]2[C:22](=[O:23])[C:21]3[CH:24]=[CH:25][CH:26]=[C:19]4[C:20]=3[C:15](=[C:16]3[CH:30]=[CH:29][CH:28]=[CH:27][C:17]3=[CH:18]4)[C:14]2=[O:31])(=O)=O)=CC=1.[CH2:33]([NH2:37])[CH2:34][CH2:35][NH2:36].[C:38](=[O:41])([O-])[O-].[Na+].[Na+]>C(#N)C>[O:31]=[C:14]1[C:15]2[C:20]3[C:19](=[CH:26][CH:25]=[CH:24][C:21]=3[C:22](=[O:23])[N:13]1[CH2:12][CH2:11][NH:36][CH2:35][CH2:34][CH2:33][NH:37][CH2:11][CH2:12][N:13]1[C:22](=[O:23])[C:21]3[CH:24]=[CH:25][CH:26]=[C:19]4[C:20]=3[C:15](=[C:16]3[CH:30]=[CH:29][CH:28]=[CH:27][C:17]3=[CH:18]4)[C:38]1=[O:41])[CH:18]=[C:17]1[CH:27]=[CH:28][CH:29]=[CH:30][C:16]1=2

Participants

5

Reactant 3

HCID 4281,3-PropanediamineHCID 10340Sodium CarbonateHCID 214604202-[2-(p-toluenesulfonyloxy)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione

Product 1

HCID 9830525HCID 9830525, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.2 g (5 mmol) of 2-[2-(p-toluenesulfonyloxy)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione, 0.4 g (2.5 mmol) of 1,3-propanediamine in 200 ml of acetonitrile is refluxed in the presence of 0.6 g (5.6 mmol) of sodium carbonate for 24 hours. The reaction mixture is concentrated in vacuo. The residue is treated with water (100 ml) and extracted with dichloromethane. The organic layers are combined, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed, eluting with dichloromethane, methanol, acetic acid (80:15:5). The appropriate fractions are combined, concentrated in vacuo and crystallized from toluene to give 0.3 g (20%) of N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-1,3-propanediamine. M.p. 191° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is treated with water (100 ml)
  3. extractionextracted with dichloromethane
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed
  8. washeluting with dichloromethane, methanol, acetic acid (80:15:5)
  9. concentrationconcentrated in vacuo
  10. customcrystallized from toluene

Sources & evidence

ORD record
ord-174aa84014b44974a43ee1df3fdb4abc
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

Loading…