tert-Butyl piperazine-1-carboxylate → HCID 69196293, Verbindung

HRID 2116517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116517
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3Cl)=[O:9])[CH:5]=[CH:6][CH:7]=1.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:24]2[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]2)=[O:9])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 69195748HCID 69195748, Verbindung

Produkt 1

HCID 69196293HCID 69196293, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A stirred suspension of (3-chlorophenyl)(8-chloro-3-quinolinyl)methanone (D5)(0.63 g, 2.1 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (0.43 g, 2.3 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.058 g, 0.064 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.074 g, 0.19 mmol) and sodium tert-butoxide (0.22 g, 2.3 mmol) in degassed toluene (3.5 ml) was heated in a sealed tube at 150° C. for 10 mins in a microwave oven. The cooled reaction mixture was washed with water (20 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to afford the title compound (D6) as a yellow foam (0.37 g, 0.81 mmol, 39%).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwas washed with water (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to an oil
  5. customThe oil was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c960b2a8cf534f5b981f39e8a5e8d3a3
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439243B2

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