N,N,N',N'-Tetramethylethylenediamine → HCID 22754314, compound

HRID 505863Notes

Reaction equation

HRID 505863 reaction equation
[CH2:1]([C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH2:3][CH3:4].CN(CCN(C)C)C.[CH2:27]([Li])[CH2:28][CH2:29][CH3:30]>C1COCC1>[CH2:1]([C:5]1([CH2:27][CH2:28][CH2:29][CH3:30])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[NH:12][C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 606127HCID 606127, compoundHCID 178418339Butyllithium

Product 1

HCID 22754314HCID 22754314, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 9-butylacridine (27.0 g, 0.115 mol) and TMEDA (4.1 mL, 0.027 mol) in THF (135 mL), was added 2.5 M n-butyllithium in hexanes (140 mL, 0.350 mol) dropwise. The mixture was stirred at 0° C. overnight and quenched with water. After stirring for an additional 0.5 hours, the reaction mixture was poured into crushed ice and extracted with ethyl acetate. The organic solution was washed with water and dried over MgSO4. The solvent was evaporated and the resulting residue was chromatographed on silica gel (hexanes:ethyl acetate=10:1 as eluent) to give 14.5 g (43%) of yellow powder.

Workup

  1. customquenched with water
  2. stirringAfter stirring for an additional 0.5 hours
  3. additionthe reaction mixture was poured
  4. custominto crushed ice
  5. extractionextracted with ethyl acetate
  6. washThe organic solution was washed with water
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated
  9. customthe resulting residue was chromatographed on silica gel (hexanes:ethyl acetate=10:1 as eluent)

Sources & evidence

ORD record
ord-8b407d645fb74d4dba7eeec9e0fd12ba
Source dataset
uspto-grants-2010_08
Patent number
US07781588B1

Reaction notes

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