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Dimethylformamide → 1-[7-(2-Methoxyethoxy)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl]-4-(4-methylphenyl)piperazine

HRID 1850500
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HRID 1850500 반응식
CN(C=O)C.[CH3:6][C:7]1([CH3:32])[CH2:11][C:10]2[C:12]([CH3:31])=[C:13]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)[C:14]([CH3:17])=[C:15]([OH:16])[C:9]=2[O:8]1.Br[CH2:34][CH2:35][O:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH3:37][O:36][CH2:35][CH2:34][O:16][C:15]1[C:9]2[O:8][C:7]([CH3:32])([CH3:6])[CH2:11][C:10]=2[C:12]([CH3:31])=[C:13]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)[C:14]=1[CH3:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 594849982,2,4,6-Tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-7-ol

생성물 1

HCID 594851191-[7-(2-Methoxyethoxy)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl]-4-(4-methylphenyl)piperazine수율 14.5%

시약·촉매·용매

2
HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of DMF (5 mL) containing 2,2,4,6-tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-7-ol (200 mg, 0.546 mmol) synthesized in Example 72, 1-bromo-2-methoxyethane (382 mg, 2.75 mmol) and potassium carbonate (380 mg, 2.75 mmol) were added, and the mixture was stirred at 100° C. for 24 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. The extract was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10) to obtain 33.5 mg of the title compound (yield 14%). Melting point was 118 to 120° C. (hexane).

후처리

  1. additionwere added
  2. temperatureAfter cooled to room temperature
  3. customThe extract was dried
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10)

출처 및 근거

ORD 기록
ord-2263fa93ab3047f9860824474911f887
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957069B2

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