Hydrochloric Acid → 2-{4-[(methylamino)methyl]-2-phenyl-1H-imidazol-1-yl}-2-phenylethanol dihydrochloride

HRID 2194716ノート

反応式

HRID 2194716 の反応式
[CH:1]([C:3]1[N:4]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:6]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11]C)=O)[CH:7]=1)=O.CO.[CH3:27][NH2:28].[BH4-].[Na+].[ClH:31].C(=O)([O-])O.[Na+]>CO>[ClH:31].[ClH:31].[CH3:27][NH:28][CH2:1][C:3]1[N:4]=[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:6]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][OH:11])[CH:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86644403methyl (4-formyl-2-phenyl-1H-imidazol-1-yl)(phenyl)acetate

生成物 1

HCID 684108602-{4-[(methylamino)methyl]-2-phenyl-1H-imidazol-1-yl}-2-phenylethanol dihydrochloride収率 27%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl (4-formyl-2-phenyl-1H-imidazol-1-yl)(phenyl)acetate (200 mg) in methanol (10 mL) was added 40% methylamine methanol solution (243 mg) and the mixture was stirred for 15 min. Sodium borohydride (71 mg) was added and the mixture was stirred for 30 min. 1 mol/L Hydrochloric acid was added to the reaction mixture and the mixture was stirred for 5 min. The mixture was neutralized with saturated sodium hydrogen carbonate solution, and extracted with ethyl acetate-tetrahydrofuran (1:1). The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→3:2) and dissolved in methanol (5 mL). A 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and insoluble materials were collected by filtration to give the title compound as a colorless powder (yield 63 mg, yield 27%).

後処理

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was stirred for 5 min
  3. extractionextracted with ethyl acetate-tetrahydrofuran (1:1)
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=1:0→3:2)
  7. dissolutiondissolved in methanol (5 mL)
  8. additionA 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  9. concentrationthe mixture was concentrated under reduced pressure
  10. additionEthyl acetate was added to the residue, and insoluble materials
  11. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-9a117ab9963e4784b56e18c242b43727
出典データセット
uspto-grants-2012_12
特許番号
US08334301B2

反応ノート

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