Cesium carbonate → 4-(4-Chloro-3-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1267916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267916
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[CH:21]=[CH:22][C:23]([Cl:24])=[C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:26])[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 144749Ethyl 5-bromo-2-chlorobenzoate

Produkt 1

HCID 536491704-(4-Chloro-3-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Piperazine-1-carboxylic acid tert-butyl ester (106 mg), 3-bromo-6-chlorobenzoic acid ethyl ester (125 mg), cesium carbonate (220 mg), palladium acetate (5 mg) and R-BINAP (22 mg) were combined in toluene (2 ml) and heated at 100° C. in a sealed vessel for 48 hr. The cooled reaction was loaded onto a silica column and eluted with iso-hexane/ethyl acetate (4:1) to give the subtitle product (170 mg).

Aufarbeitung

  1. customThe cooled reaction
  2. washeluted with iso-hexane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f63c3d2e23c54986ae9032bf5396e921
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555541B1

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