Ethylene Glycol → 3-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine

HRID 70572노트

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HRID 70572 반응식
[CH2:1]([OH:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2([CH2:25][CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[O:4][CH2:1][CH2:2][O:3]2)=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate2회HCID 128598381-(4-Bromophenyl)-4-(diethylamino)butan-1-one

생성물 1

HCID 584524843-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine수율 91%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
150 °C

실험 절차

Ethylene glycol (10 mL) and p-toluenesulfonic acid monohydrate (128 mg) were added to a solution of 1-(4-bromophenyl)-4-(diethylamino)butan-1-one (2.0 g) in toluene (80 mL), and the mixture was stirred at 150° C. for one hour. The reaction solution was cooled to room temperature and p-toluenesulfonic acid monohydrate (1.28 g) was added, after which the mixture was stirred at 150° C. for further one hour. The reaction solution was cooled to room temperature and neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound as a brown oil (2.09 g, 91%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringafter which the mixture was stirred at 150° C. for further one hour
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-d04b8a6eb8924dedad28ee4afc3226fb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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