Potassium Iodide → HCID 67853859, compound

HRID 847412Notes

Reaction equation

HRID 847412 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]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[ClH:1].[CH2:29]([NH:36][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][CH2:6][C:19]2[CH:18]=[CH:17][CH:12]=[CH:11][CH:10]=2)=[CH:8][CH:7]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 1218099,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

Product 1

HCID 67853859HCID 67853859, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-bis-(3-chloro-2-hydroxypropylamino)-9, 10-anthracenedione (1 g, 2.36 mmole), benzylamine (2.02 g, 18.88 mmole), and potassium iodide (0.25 g, 153 mmole) in a solution of methanol (40 mL) and dichloromethane (5 mL), which had been heated at reflux for 5 hours, was added potassium carbonate (0.7 g, 5.06 mmole). The reaction was heated at reflux for an additional 16 hours. Solvent was removed and the blue product was dissolved in dichloromethane and washed three times with water. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The blue free base product was purified by column chromatography (silica gel, dichloromethane with an increasing methanol gradient). The title product 1,4-Bis-(3-Benzylamino-2-Hydroxypropylamino)-9, 10 anthracenedione. Hydrochloride salt (610 mg, 42% yield) was formed by bubbling hydrochloride gas through a stirring solution of the free base in acetone until a color change was noted, mp 86°-89° C.; NMR (CDCl3) δ 2.76 (m, 2H, CH2) 2.90 (m, 2H CH2), 3.43 (m, 6H, CH2 and OH), 3.85 (d, J=4.3 Hz, 4H, CH2), 4.04 (m, 2H, CH), 7.15 (s, 2H, Ar (2, 3)), 7.31 (m, 10H, Ar (Benzyl)), 7.64 (m, 2H, Ar (6 ,7)), 8.22 (m, 2H, Ar (5, 8)), 10.82 (b, 2H, NH); Anal. Calcd for C34H37N4O4 ×HCl: C, 67.93; H, 6.20; N, 9.32. Found: C, 68.21; H, 6.14; N, 9.02.

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureThe reaction was heated
  3. temperatureat reflux for an additional 16 hours
  4. customSolvent was removed
  5. dissolutionthe blue product was dissolved in dichloromethane
  6. washwashed three times with water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe blue free base product was purified by column chromatography (silica gel, dichloromethane with an increasing methanol gradient)

Sources & evidence

ORD record
ord-40a5fafcf0764fffaa6dedf6c51914c3
Source dataset
uspto-grants-1992_08
Patent number
US05141957

Reaction notes

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