N,N,N',N'-Tetramethylethylenediamine → HCID 606127, compound

HRID 505862Notes

Reaction equation

HRID 505862 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.CN(C)CCN(C)C.[CH2:23]([Li])[CH2:24][CH2:25][CH3:26].[OH-].[K+]>C1COCC1.C(#N)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH2:23]([C:13]1[C:14]2[C:5]([N:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 9215AcridineHCID 14797Potassium HydroxideHCID 178418339Butyllithium

Product 1

HCID 606127HCID 606127, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of acridine (24.8 g, 0.139 mol) and TMEDA (N,N,N′,N′-tetramethylethylenediamine) (5.0 ml, 0.034 mol) in THF (160 mL), was slowly added 2.5 M n-butyllithium in hexanes (162 mL, 0.405 mol). The resulting solution was stirred at 0° C. for 2 hours and quenched with water. After stirring for an additional 0.5 hour, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water several times and dried over MgSO4. Removal of solvent afforded a residue. This residue was taken up in acetonitrile (700 mL) and treated with potassium ferricyanide (198.0 g, 0.601 mol) aqueous solution (1110 mL) containing potassium hydroxide (99.0 g, 1.764 mol) for about 42 hours at room temperature. The mixture was extracted with ethyl acetate and dried over MgSO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (hexanes:ethyl acetate=10:1 as eluent) to afford 27.0 g (83%) of yellow powder.

Workup

  1. customquenched with water
  2. stirringAfter stirring for an additional 0.5 hour
  3. additionthe reaction mixture was poured into ice-water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water several times
  6. dry with materialdried over MgSO4
  7. customRemoval of solvent
  8. customafforded a residue
  9. extractionThe mixture was extracted with ethyl acetate
  10. dry with materialdried over MgSO4
  11. customAfter evaporation of the solvent
  12. customthe crude product was purified by chromatography on silica gel (hexanes:ethyl acetate=10:1 as eluent)

Sources & evidence

ORD record
ord-19778d7870ad47908f28fb886a4891e0
Source dataset
uspto-grants-2010_08
Patent number
US07781588B1

Reaction notes

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