Potassium Carbonate → HCID 54531367, Verbindung

HRID 582551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582551
[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].Br[CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][CH2:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 54247840HCID 54247840, Verbindung

Produkt 1

HCID 54531367HCID 54531367, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-(tert-butyloxycarbonyl)piperazine (1.73 g, 9.3 mmol), 4-bromo-4-phenylbutyronitrile (2.5 g, 11 mmol) and K2CO3 (1.4 g, 10.2 mmol) in DMF (40 mL) was heated at 60° C. for 4 h. After this time the mixture was cooled to room temperature, filtered and the filtrate evaporated. The residue was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (2:1). The piperazine (2.69 g, 88%) was isolated as a pale yellow oil, which solidified on standing in the fridge. 1H NMR (250 MHz, CDCl3) δ1.41 (9H, s), 1.94-2.46 (8H, m), 3.32-3.60 (5H, m), 7.15-7.42 (5H, m). MS (ES+) (330, M+1).

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with petrol:EtOAc (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-df2973ac3e554307beb29dee16328407
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925638

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