Potassium Carbonate → Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate

HRID 383820

Reaktionsgleichung

Reaktionsgleichung von HRID 383820
[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28](=O)[CH2:29]Br)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]>C(#N)C>[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][CH2:29][N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:22]([CH3:27])([CH3:23])[CH3:21])=[O:8])[CH2:2][CH2:3]3)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 131766Piperazine-1-carboxylic acidHCID 197113291-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

Produkt 1

HCID 59636762Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of piperazine-1-carboxylic acid tent-butyl ester (0.750 g, 4.03 mmol) in dry acetonitrile (20 mL) grounded potassium carbonate (0.486 mL, 8.05 mmol) was added followed by the product mixture from Example 38a (1.134 g) and the reaction was heated at 70° C. under argon over night. The acetonitrile was evaporated and DCM and water was added. The layers were separated and the aq phase was extracted with DCM (3×). The combined organic phases were dried (Na2SO4), filtered and evaporated. The crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100) to give 0.823 g (55%) of the title compound.

Aufarbeitung

  1. additionwas added
  2. customThe acetonitrile was evaporated
  3. additionDCM and water was added
  4. customThe layers were separated
  5. extractionthe aq phase was extracted with DCM (3×)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100)

Quellen und Nachweise

ORD-Eintrag
ord-f0b72abc57aa416888c498f997519efe
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367676B2

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