Potassium Iodide → HCID 67853860, compound

HRID 847411Notes

Reaction equation

HRID 847411 reaction equation
[Cl:1][CH2:2][CH:3]([OH:28])[CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([NH:22][CH2:23][CH:24]([OH:27])[CH2:25]Cl)=[CH:8][CH:7]=1.[CH2:29]([NH2:32])[CH2:30][CH3:31].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CO>[ClH:1].[CH2:29]([NH:32][CH2:2][CH:3]([OH:28])[CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([NH:22][CH2:23][CH:24]([OH:27])[CH2:25][NH:5][CH2:4][CH2:3][CH3:2])=[CH:8][CH:7]=1)[CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7852PropylamineHCID 11430Potassium CarbonateHCID 1218099,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

Product 1

HCID 67853860HCID 67853860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-bis-(3-chloro-2-hydroxylpropylamino)-9, 10-anthracenedione (1 g, 2.36 mmole), propylamine (1.39 g, 23.6 mmole), and potassium iodide (0.26 g, 160 mmole) in methanol (20 mL), which had been stirred for 4 hours at room temperature, was added potassium carbonate (0.5 g, 3.62 mmole), and the reaction was stirred at room temperature for an additional 16 hours. Solvent was removed and the blue product was dissolved in dichloromethane, and was washed three times with water. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The blue product was purified by column chromatography (silica gel, dichloromethane with an increasing methanol gradient) to yield the free base of the title compound, which was then treated with hydrochloride gas through a stirring solution in acetone until a color change was noted to yield the title compound 1,4-Bis-(3-Propylamino-2-Hydroxypropylamino)-9, 10 anthracenedione hydrochloride (580 mg, 48%); NMR (CDCl3) δ 0.94 (t, J=7.3 Hz, 6H, CH3), 1.57 (m, 4H, CH2), 2.64 (m, 4H, CH2), 2.75 (m, 4H, CH2), 3.33 (m, 6H, CH and CH2), 4.05 b, 2H, OH), 6.80 (s, 2H, Ar (2, 3)), 7.52 (m, 2H, Ar (6, 7)), 7.94 (m, 2H, Ar (5, 8)), 10.63 (b, 2H, NH);

Workup

  1. customSolvent was removed
  2. dissolutionthe blue product was dissolved in dichloromethane
  3. washwas washed three times with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe blue product was purified by column chromatography (silica gel, dichloromethane with an increasing methanol gradient)

Sources & evidence

ORD record
ord-83d2f3af32c8421e9e594c730b4dbdf6
Source dataset
uspto-grants-1992_08
Patent number
US05141957

Reaction notes

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