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Sodium Hydroxide → N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride

HRID 655664
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HRID 655664 반응식
[ClH:1].[Na].Cl.[S:4]1[CH:8]=[CH:7][C:6]2[C:9]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([CH3:29])=[CH:27][C:26]([NH:30][CH:31]=O)=[CH:25][C:24]=4[O:33][CH3:34])[CH2:15][CH2:14]3)=[CH:10][CH:11]=[CH:12][C:5]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[ClH:1].[CH3:31][NH:30][C:26]1[CH:27]=[C:28]([CH3:29])[C:23]([O:22][CH2:21][CH2:20][CH2:19][N:16]2[CH2:17][CH2:18][N:13]([C:9]3[C:6]4[CH:7]=[CH:8][S:4][C:5]=4[CH:12]=[CH:11][CH:10]=3)[CH2:14][CH2:15]2)=[C:24]([O:33][CH3:34])[CH:25]=1
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참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23872008Sodium hydrochlorideHCID 574995784-[3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl formamide hydrochloride

생성물 1

HCID 16044808N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride

시약·촉매·용매

2
HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A 6N aqueous sodium hydrochloride solution was added to N-(4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl formamide hydrochloride (0.23 g, 0.48 mmol) and the solution mixture was extracted with dichloromethane. The extraction solution with dichloromethane was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in a tetrahydrofuran (THF) solution (5 ml) and lithium aluminum hydride (30 mg, 0.71 mmol) was added thereto under ice cooling and refluxed with heating for 15 minutes. The reaction solution was cooled on ice, and water (0.03 ml), 15% aqueous sodium hydroxide solution (0.03 ml), and water (0.09 ml) were added to the reaction mixture in this order and stirred. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1) and concentrated under reduced pressure. A solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue, and the insoluble matter precipitated was obtained by filtration to obtain N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline hydrochloride (63 mg) as white powder.

후처리

  1. extractionthe solution mixture was extracted with dichloromethane
  2. dry with materialThe extraction solution with dichloromethane was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionwas added
  5. temperatureunder ice cooling and refluxed
  6. temperaturewith heating for 15 minutes
  7. additionwere added to the reaction mixture in this order
  8. customInsoluble matter was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→3:1)
  11. concentrationconcentrated under reduced pressure
  12. additionA solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue
  13. customthe insoluble matter precipitated
  14. customwas obtained by filtration

출처 및 근거

ORD 기록
ord-cb9fed83f42442ccbbc382f15cc1a88d
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071600B2

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