Potassium Carbonate → 2'-(Benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4'-fluoroacetophenone

HRID 1433150

Reaktionsgleichung

Reaktionsgleichung von HRID 1433150
[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:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:32])[CH2:30]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:32])[CH2:30][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 579348132'-(Benzyloxy)2-bromo4'-fluoroacetophenone

Produkt 1

HCID 690593352'-(Benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4'-fluoroacetophenoneAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(tert-Butoxycarbonyl)piperazine (808 mg, 4.34 mmol) was added to a mixture of 2′-(benzyloxy)-2-bromo4′-fluoroacetophenone (assumed 4.13 mmol) and potassium carbonate (856 mg, 6.20 mmol) in DMF, and stirred for 18 h at room temperature. The solvent was removed in vacuo, the residue taken up in ethyl acetate (150 mL) and washed with water (100 mL) and brine (100 mL). The organice layer was dried (MgSO4) and the solvents removed in vacuo. The crude product was purified by flash chromatography, eluting with 9:1 hexane:EtOAc followed by 1:1 hexane:EtOAc to give pure 2′-(benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4′-fluoroacetophenone (1.42 g, 80% over 2 steps) as a yellow oil; Rf 0.00 (9:1 hexane:EtOAc), 0.50 (1:1 hexane:EtOAc); δH (CDCl3) 7.89 (1H, dd, J=9.3 and 6.9 Hz), 7.48-7.44 (5H, m), 6.81-6.77 (2H, m), 5.17 (2H, s), 3.79 (2H, s), 3.51-3.47 (4H, m), 2.44-2.41 (4H, m), 1.50 (9H, s); LCMS retention time 2.10 min, M+H+ 429.4.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialThe organice layer was dried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customThe crude product was purified by flash chromatography
  6. washeluting with 9:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-f03db8d5639144f7af01926186f81cb1
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612201B2

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