4-[Benzyl(methyl)amino]cyclohexan-1-one → 4-(Benzyl(methyl)amino)-1-(2-(dimethylamino)pyridin-4-yl)cyclohexanol

HRID 1193403ノート

反応式

HRID 1193403 の反応式
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:15])[CH3:14])[CH:8]=1.[CH2:16]([N:23]([CH3:31])[CH:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)C>[CH2:16]([N:23]([CH3:31])[CH:24]1[CH2:29][CH2:28][C:27]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]([CH3:15])[CH3:14])[CH:8]=2)([OH:30])[CH2:26][CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 220099204-[Benzyl(methyl)amino]cyclohexan-1-oneHCID 234369354-Bromo-N,N-dimethylpyridin-2-amineHCID 178418339Butyllithium

生成物 1

HCID 667992224-(Benzyl(methyl)amino)-1-(2-(dimethylamino)pyridin-4-yl)cyclohexanol収率 71%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

n-BuLi (3 ml, 5.98 mmol, 1.2 eq., 2 M solution in hexane) was added at −78° C. to a solution of 4-bromo-N,N-dimethylpyridin-2-amine (978 mg, 5.23 mmol, 1.05 eq.) in diethyl ether (15 ml) and the mixture was stirred for 45 minutes. A solution of 4-(benzyl(methyl)amino)cyclo-hexanone (stage 3, AMN-50) (1.08 g, 4.9, 8 mmol 1.0 eq.) in diethyl ether (10 ml) was added dropwise thereto at the same temperature. The reaction mixture was stirred for 16 hours at RT and was then hydrolyzed with sat. ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×60 ml). The combined org. phases were washed with sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated and purified by column chromatography (silica gel, 2,5% MeOH in DCM). Yield: 71% (1.20 g, 3.54 mmol)

後処理

  1. stirringThe reaction mixture was stirred for 16 hours at RT
  2. extractionhydrolyzed with sat. ammonium chloride solution (30 ml) and extracted with ethyl acetate (3×60 ml)
  3. washphases were washed with sat. NaCl solution (100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, 2,5% MeOH in DCM)

出典と根拠

ORDレコード
ord-cdc17ed0fd8346a1a39954acc13f5bbc
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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