6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamide → 1-[2-[(6-aminohexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

HRID 845473노트

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HRID 845473 반응식
[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:16])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:16][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH:7]([CH2:17][O:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

4

반응물 2

HCID 201311496-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 201311911-[2-[(6-aminohexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

6-[2-(1H-Imidazol-1-yl)-1[[4-methoxyphenyl)methoxy]methyl]ethoxy]hexanamide (Example 20, 0.3 g, 0.0008 mol) in dry tetrahydrofuran (2 ml) was added to a stirred suspension of lithium aluminium hydride (0.5 g, 0.013 mol) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere. The resulting suspension was stirred under reflux for 24 hours cooled to room temperature and the residual lithium aluminium hydride destroyed using ethyl acetate (15 ml) followed by dilute sodium hydroxide solution (2N, 20 ml), the resulting solution was filtered and the filter cake was washed with ethyl acetate (50 ml), the organic layer was separated, dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica gel, ethylacetate to 10% methanol in ethyl acetate) to yield the title compound as an oil.

후처리

  1. temperatureunder reflux for 24 hours
  2. customthe residual lithium aluminium hydride destroyed
  3. filtrationthe resulting solution was filtered
  4. washthe filter cake was washed with ethyl acetate (50 ml)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated to an oil which
  8. customwas purified by column chromatography (silica gel, ethylacetate to 10% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-fd87b5f3526b4cd7aa3e2e3df1a43693
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04758573

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