Dichloromethane → Cis-N-[2-Methyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydroquinolin-4-yl]-N-phenyl-acetamide

HRID 1352503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352503
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:10][CH:11]1[CH2:20][CH:19]([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1.C(N(C(C)C)C(C)C)C.ClCCl>O1CCOCC1>[CH3:10][C@H:11]1[CH2:20][C@@H:19]([N:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:24])[CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:8]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 82604Nicotinoyl chlorideHCID 2837129N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide

Produkt 1

HCID 69425438Cis-N-[2-Methyl-1-(pyridine-3-carbonyl)-1,2,3,4-tetrahydroquinolin-4-yl]-N-phenyl-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Nicotinoyl chloride (1.1 eq) was added to a solution of N-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenylacetamide (100 mg) and N-ethyl-N,N-diisopropylamine (2.2 eq) in dioxane (1 ml). The mixture was stirred overnight at room temperature. Dichloromethane was added and the organic layer was washed by water and sodium carbonate solution and dried over sodium sulfate. The solvent was removed and the mixture was purified by chromatography on silica gel (dichloromethane and ethanol (99:1)) to afford the title compound (30 mg).

Aufarbeitung

  1. washthe organic layer was washed by water and sodium carbonate solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed
  4. customthe mixture was purified by chromatography on silica gel (dichloromethane and ethanol (99:1))

Quellen und Nachweise

ORD-Eintrag
ord-0d3e24c587bd42deab3a75a86b6169e3
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220760B2

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