1,2-Dichloroethane → HCID 45257316, Verbindung

HRID 1510060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510060
[Cl:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]2[C:9]([C:10]=1[C:11](O)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[C:29]([O:28][C:26]([N:20]1[CH2:25][CH2:24][N:23]([C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:2]=2[Cl:1])=[O:12])[CH2:22][CH2:21]1)=[O:27])([CH3:32])([CH3:31])[CH3:30]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 995242-Chloro-1-phenyl-1H-indole-3-carboxylic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 181649HOAt

Produkt 1

HCID 45257316HCID 45257316, VerbindungAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-1-phenyl-1H-indole-3-carboxylic acid (cf. CA 1079739) (3.00 g, 11.0 mmol), tert-butyl 1-piperazinecarboxylate (2.06 g, 11.0 mmol), EDC (2.33 g, 12.1 mmol) and HOAT (1.73 g, 12.7 mmol) in DMF (12 ml) was added NMM (3.65 ml, 33.1 mmol), and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (EA/HEP 1:3). 4.51 g of the title compound were obtained.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (EA/HEP 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-e06ce66d7f9340c59168a5b30bd7d9f8
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211885B2

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