Water → tert-Butyl 4-(4-nitroanilino)piperidine-1-carboxylate

HRID 1791908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791908
NN1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[CH:25]([N:28](CC)C(C)C)(C)C.O>CN1CCCC1=O>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:25]([NH:28][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:12])([CH3:13])[CH3:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 22029174tert-Butyl 4-aminopiperazine-1-carboxylate

Produkt 1

HCID 22028451tert-Butyl 4-(4-nitroanilino)piperidine-1-carboxylateAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Amino-1-tert-butoxycarbonylpiperazine (3.00 g), 4-fluoronitrobenzene (2.54 g) and N,N-diisopropylethylamine (8.82 g) were dissolved in N-methyl-2-pyrrolidone (30 mL), and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was added to water and the mixture was extracted with ethyl acetate. The extract was washed with brine and dried. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 1-tert-butoxycarbonyl-4-(4-nitrophenyl)aminopiperidine (2.55 g) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cdc8330fdabf4b8090f409cf85b62274
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074794B2

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