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

HRID 1193403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193403
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

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)

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cdc17ed0fd8346a1a39954acc13f5bbc
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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