Dimethylformamide → HCID 18509504, compound

HRID 1356831Notes

Reaction equation

HRID 1356831 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9]CN)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:23]=[C:24]([C:28](=[O:30])[CH3:29])[CH:25]=[CH:26][CH:27]=1.[CH3:31][N:32](C)C=O>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:32]([CH2:21][C:22]2[CH:23]=[C:24]([C:28](=[O:30])[CH3:29])[CH:25]=[CH:26][CH:27]=2)[CH3:31])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 27356892-(4-Tert-butylphenyl)ethan-1-amineHCID 154798071-(3-(Bromomethyl)phenyl)ethan-1-one

Product 1

HCID 18509504HCID 18509504, compoundYield 65.2%

Procedure

N-(4-tert-butylbenzyl)methylamine (1.25 g; 7.04 mmol) and potassium carbonate (1.95 g; 14.1 mmol) were added to N,N-dimethylformamide (30 ml). While the mixture was stirred in an ice bath, 3′-bromomethylacetophenone (1.50 g; 7.04 mmol) in N,N-dimethylformamide (10 ml) was added dropwise. After completion of the addition, the mixture was removed from the ice bath, and stirred for 1 hour at room temperature. Reaction was stopped by pouring the mixture into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform), to thereby yield 1.42 g of the target compound as pale yellow oily matter (yield: 65.2%).

Workup

  1. additionAfter completion of the addition
  2. customthe mixture was removed from the ice bath
  3. stirringstirred for 1 hour at room temperature
  4. customReaction
  5. additionby pouring the mixture into ice+saturated aqueous sodium bicarbonate solution
  6. extractionfollowed by extraction with ethyl acetate (100 ml)
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  8. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-a36f102d6ee240d0a0cc1b15cf92ac0f
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

Loading…