Sodium Carbonate → HCID 68461115, Verbindung

HRID 2055811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055811
Br[C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7]C)=[O:5].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[Na+].[Na+]>C(O)CCC>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3731400Ethyl 2-bromo-3-nitrobenzoate

Produkt 1

HCID 68461115HCID 68461115, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 736 mg (2.83 mmol) of ethyl 2-bromo-3-nitrobenzoate and 579 mg (3.1 mmol, 1.1 eq) of 1-tert-butyloxycarbonylpiperazine in n-butanol (6 mL) was added 330 mg (3.1 mmol, 1.1 eq) of Na2CO3. The mixture was heated to reflux for 4 h. The solvent was removed under reduced pressure. The crude product was partitioned between EtOAc (100 mL) and 20 mL of H2O. The organic layer was washed with H2O (2×20 mL), dried over Na2SO4 and concentrated. Column chromatography (silica, 10-20% EtOAc/hexanes) provided 744 mg (72%) of 4-(2-methoxycarbonyl-6-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. TLC (silica, 20% EtOAc/hexanes): Rf=0.5. 1H NMR (400 MHz, CDCl3): 7.67 (dd, J=8.2, 1.4 Hz, 1H), 7.62 (dd, J=8.2, 1.4 Hz, 1H), 7.16 (t, J=8.2 Hz, 1H), 3.86 (s, 3H), 3.44-3.36 (m, 4H), 3.03-2.95 (m, 4H), 1.48 (s, 9H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed under reduced pressure
  4. customThe crude product was partitioned between EtOAc (100 mL) and 20 mL of H2O
  5. washThe organic layer was washed with H2O (2×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2775f3debe8644ab83cd242a93925381
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332494B2

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