1,4-Dioxane → HCID 59497138, compound

HRID 2046529Notes

Reaction equation

HRID 2046529 reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:11](=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[N:13]3)[N:10]=[C:9]([CH3:21])[CH:8]=1)[CH3:2].[O:24]1CCOCC1>O>[CH2:22]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[C:20]2[C:11](=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[N:13]3)[N:10]=[C:9]([CH:21]=[O:24])[CH:8]=1)[CH3:23]

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 59497147HCID 59497147, compound

Product 1

HCID 59497138HCID 59497138, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of SeO2 (0.83 g, 7.5 mmol) in a mixture of dioxane (38 mL) and water (3 mL) was heated to reflux in a two-neck 100 mL round-bottomed flask. A solution of diethyl-[2-(2-methyl-[1,10]phenanthrolin-4-yloxy)-ethyl]amine (0.93 g, 3.0 mmol) in hot dioxane (20 mL) was added through an addition funnel over a period of 15 minutes and the reaction mixture was refluxed for 45 minutes. The solvent was evaporated in vacuo and the residue was treated with methylene chloride (100 mL) and saturated NaHCO3 (100 mL). The aqueous layer was extracted with methylene chloride (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:40) to afford the pure material as a brown solid (0.19 g, 19%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a two-neck 100 mL round-bottomed flask
  3. temperaturethe reaction mixture was refluxed for 45 minutes
  4. customThe solvent was evaporated in vacuo
  5. additionthe residue was treated with methylene chloride (100 mL) and saturated NaHCO3 (100 mL)
  6. extractionThe aqueous layer was extracted with methylene chloride (3×100 mL)
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:40)

Sources & evidence

ORD record
ord-2803435c4eef495bbd50415c9401d936
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

Loading…