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Sodium hydride → 1-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}-1-(2-dimethylaminoethyl)indol-2-ylcarbonyl}-4-(2-chlorophenyl)-piperazine

HRID 442849
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HRID 442849 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:25][CH2:24]2)=[O:22])=[CH:7][CH:6]=1.[H-].[Na+].Cl.[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:52][CH2:51][N:50]([CH3:54])[CH3:49])[C:13]=2[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:25][CH2:24]2)=[O:22])=[CH:9][CH:10]=1
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참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 158589011-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine

생성물 1

HCID 701465951-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}-1-(2-dimethylaminoethyl)indol-2-ylcarbonyl}-4-(2-chlorophenyl)-piperazine
수율 94.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of Compound 1 (2.0 g, 3.19 mmol) obtained in Example 1 in 30 ml of N,N-dimethylformamide was portionwise added sodium hydride (60% in oil, 270 mg, 6.71 mmol) with stirring at 0° C., and 2-dimethylaminoethylchloride hydrochloride (460 mg, 3.19 mmol) was added thereto, followed by heating to 80° C. and then stirring for one hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution for neutralization, and water was added thereto followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give 2.9 g of a crude product. The obtained crude product was purified with silica gel column chromatography (ethyl acetate/hexane=1/1-ethyl acetate alone) to give 2.1 g (yield: 94%) of the title compound.

후처리

  1. temperatureby heating to 80° C.
  2. stirringstirring for one hour
  3. additionwas added
  4. extractionthereto followed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto give 2.9 g of a crude product
  9. customThe obtained crude product
  10. customwas purified with silica gel column chromatography (ethyl acetate/hexane=1/1-ethyl acetate alone)

출처 및 근거

ORD 기록
ord-6eecc990e763474fa5080fd0b25b37a3
출처 데이터셋
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05891902

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