Dimethylformamide → 4-ethenyl-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 1850380노트

반응식

HRID 1850380 반응식
Br[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Br)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+].CN(C=O)C.[NH2:26][C:27]1[C:28]([CH3:42])=[C:29]([CH3:41])[C:30]2[O:34][C:33]([CH3:36])([CH3:35])[C:32](=[O:37])[C:31]=2[C:38]=1[CH:39]=[CH2:40]>C(OCC)(=O)C.O>[CH:39]([C:38]1[C:31]2[C:32](=[O:37])[C:33]([CH3:35])([CH3:36])[O:34][C:30]=2[C:29]([CH3:41])=[C:28]([CH3:42])[C:27]=1[N:26]1[CH2:14][CH2:13][N:4]([C:5]2[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1)=[CH2:40]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 667591945-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-oneHCID 66759772N,N-bis(2-bromoethyl)-4-methoxyaniline

생성물 1

HCID 667602304-ethenyl-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one수율 8.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

N,N-bis(2-bromoethyl)-4-methoxyaniline (2.45 g, 7.63 mmol) and sodium hydrogencarbonate (1.25 g, 1.40 mmol) were added to a solution of DMF (36 mL) containing 5-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (1.47 g, 6.36 mmol) synthesized in Reference Example 22, and the mixture was stirred at 120° C. for 16 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 100:0 to 90:10) to give 217 mg of the title compound (yield: 8%).

후처리

  1. customsynthesized in Reference Example 22
  2. temperatureAfter cooled to room temperature
  3. customIt was dried
  4. customAfter that, the solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 100:0 to 90:10)

출처 및 근거

ORD 기록
ord-bee36db59ff64b9d81f88184aa934cdb
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957069B2

반응 노트

불러오는 중…