Potassium Carbonate → 3'-[N-(4-tert-Butylbenzyl)-N-cyclopropylaminomethyl]acetophenone

HRID 1356836Notes

Reaction equation

HRID 1356836 reaction equation
[CH:1]1([NH:4][CH2:5][C:6]2[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:21]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([CH2:29][N:4]([CH2:5][C:6]2[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH:1]2[CH2:2][CH2:3]2)=[CH:31][CH:32]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 185094213'-(N-Cyclopropylaminomethyl)acetophenone

Product 1

HCID 185095303'-[N-(4-tert-Butylbenzyl)-N-cyclopropylaminomethyl]acetophenoneYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3′-(N-cyclopropylaminomethyl)acetophenone (0.30 g; 1.59 mmol) and potassium carbonate (0.31 g; 2.27 mmol) were added to N,N-dimethylformamide (15 ml). While the mixture was stirred at room temperature, 4-tert-butylbenzyl bromide (0.29 g; 1.51 mmol) in N,N-dimethylformamide (5 ml) was added dropwise. The mixture was stirred for 1 hour at room temperature, and the 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 (n-hexane:ethyl acetate=15:1), to thereby yield 0.20 g of the target compound as colorless transparent oily matter (yield: 39.5%).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. additionby pouring the mixture into ice+saturated aqueous sodium bicarbonate solution
  3. extractionfollowed by extraction with ethyl acetate (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-939cf9f1eee9476ab5a84ecfcfee6be6
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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