Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 4-[(2-amino-3-fluoro-5-methoxyphenyl)amino]-1-piperidinecarboxylate

HRID 447765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447765
[N+:1]([C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 596832591,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidinecarboxylate

Produkt 1

HCID 596832781,1-Dimethylethyl 4-[(2-amino-3-fluoro-5-methoxyphenyl)amino]-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidine-carboxylate (D12) (380 mg, 1 mmol) was dissolved in ethanol (10 ml) and Raney nickel (50% aqueous suspension, 1 ml) was added at room temperature; the mixture was heated to 40° C. and hydrazine monohydrate (0.5 ml) was added over dropwise. After 30 min more, the reaction mixture was cooled to room temperature, filtered through Celite and the solvent evaporated. The product was purified by silica gel chromatography eluting with 20 to 50% ethyl acetate in hexane to yield the title compound, 250 mg. M+-H=340.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customthe solvent evaporated
  4. customThe product was purified by silica gel chromatography
  5. washeluting with 20 to 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-855ec3348ecb43a0b4b98337bb3dbaa0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481566B2

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