4-bromo-N,N-dimethylaniline → HCID 11333766, compound

HRID 378239Notes

Reaction equation

HRID 378239 reaction equation
C([Li])CCC.Br[C:7]1[CH:15]=[CH:14][C:10]([N:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=1.CN(OC)[C:18](=[O:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH3:12][N:11]([CH3:13])[C:10]1[CH:14]=[CH:15][C:7]([C:18](=[O:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 114654-bromo-N,N-dimethylanilineHCID 13642088N-Methoxy-N-methylheptanamideHCID 178418339Butyllithium

Product 1

HCID 11333766HCID 11333766, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5 M in hexanes, 51 mL, 127 mmol) was added dropwise to 4-bromo-N,N-dimethylaniline (23.1 g, 115 mmol, Aldrich Chemical Co.) in anhydrous THF at -78° C. After 10 min. a solution of N-methyl-N-methoxyheptanamide (10.0 g, 57.7 mmol) in 20 mL THF was added dropwise via canula. The reaction was allowed to proceed 1 hr., then quenched with 1 N aq. HCl and carefully poured into sat. NaHCO3. The aqueous layer was extracted with ethyl ether, and the combined organic fraction was washed with water, brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (15% EtOAc/hexanes) yielded 1-(4-dimethylaminophenyl)heptan-1-one as a yellow solid (6.49 g, 48%). MS 234 (M+H)+.

Workup

  1. custom, then quenched with 1 N aq. HCl
  2. additioncarefully poured into sat. NaHCO3
  3. extractionThe aqueous layer was extracted with ethyl ether
  4. washthe combined organic fraction was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03151e11241f452182984598ce47b026
Source dataset
uspto-grants-2000_02
Patent number
US06030969

Reaction notes

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