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

HRID 1356836노트

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HRID 1356836 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-939cf9f1eee9476ab5a84ecfcfee6be6
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586633B1

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