Potassium Carbonate → HCID 12069881, compound

HRID 1356778Notes

Reaction equation

HRID 1356778 reaction equation
[CH3:1][C:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH:5]=[CH:6][CH2:7][NH:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:21]=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][CH:25]=1>CN(C)C=O>[CH3:1][C:2]([CH3:11])([CH3:10])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:19][C:20]1[CH:21]=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][CH:25]=1)[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154798071-(3-(Bromomethyl)phenyl)ethan-1-oneHCID 53427009N,6,6-trimethylhept-2-en-4-yn-1-amine

Product 1

HCID 12069881HCID 12069881, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-(6,6-dimethyl-2-hepten-4-ynyl)methylamine (trans:cis=about 3:1) (1.06 g; 7.04 mmol) and potassium carbonate (1.95 g; 14.1 mmol) were added to N,N-dimethylformamide (20 ml). While the mixture was stirred in an ice bath, 3′-bromomethylacetophenone (1.31 g; 6.15 mmol) in N,N-dimethylformamide (15 ml) was added dropwise. After completion of addition, the mixture was removed from the ice bath, and stirred for 15 minutes 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 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 1.54 g of the target compound (yield: 88.4%).

Workup

  1. additionAfter completion of addition
  2. customthe mixture was removed from the ice bath
  3. stirringstirred for 15 minutes 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 and with saturated brine
  8. dry with materialdried 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-4faa815e8eb74af58f597ee1b38fdc0e
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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