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

HRID 1193403노트

반응식

HRID 1193403 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-cdc17ed0fd8346a1a39954acc13f5bbc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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