Diethylethanolamine → HCID 59497147, compound

HRID 2046528Notes

Reaction equation

HRID 2046528 reaction equation
[H-].[Na+].[CH2:3]([N:5]([CH2:8][CH2:9][OH:10])[CH2:6][CH3:7])[CH3:4].Cl[C:12]1[C:25]2[C:16](=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[CH:20][CH:19]=[N:18]3)[N:15]=[C:14]([CH3:26])[CH:13]=1>C1COCC1>[CH2:3]([N:5]([CH2:6][CH3:7])[CH2:8][CH2:9][O:10][C:12]1[C:25]2[C:16](=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[CH:20][CH:19]=[N:18]3)[N:15]=[C:14]([CH3:26])[CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 59497129HCID 59497129, compound

Product 1

HCID 59497147HCID 59497147, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (60% in mineral oil, 5.25 g, 131.1 mmol) in anhydrous THF (90 mL) a solution of N,N-diethyl-2-hydroxyethylamine (15.30 g, 131.1 mmol) in anhydrous THF (60 mL) was slowly added. The mixture was stirred at room temperature for 20 minutes and a solution of 4-chloro-2-methyl-[1,10]phenanthroline(6.00 g, 26.2 mmol) in anhydrous THF (90 mL) was slowly added. The reaction mixture was refluxed for 18 hours and then allowed to cool down to room temperature, quenched with 1N HCl and evaporated. The residue was redissolved in 1N NaOH (150 mL) and extracted with methylene choride (3×200 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was washed with hexane and purified by flash chromatography (SiO2, MeOH/DCM, 1:40) to yield the pure product as an orange oil (5.1 g, 63%).

Workup

  1. additionwas slowly added
  2. temperatureThe reaction mixture was refluxed for 18 hours
  3. temperatureto cool down to room temperature
  4. customquenched with 1N HCl
  5. customevaporated
  6. dissolutionThe residue was redissolved in 1N NaOH (150 mL)
  7. extractionextracted with methylene choride (3×200 mL)
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. washThe residue was washed with hexane
  12. custompurified by flash chromatography (SiO2, MeOH/DCM, 1:40)

Sources & evidence

ORD record
ord-a61f5da5f9c648779aad3cbb3257a50e
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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