4-(2,6-Difluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester → 4-(4-Amino-2,6-difluorophenyl)piperazine, N1-BOC protected

HRID 77428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77428
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([F:24])=[CH:16][C:17]([NH2:21])=[CH:18][C:19]=2[F:20])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 214626024-(2,6-Difluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester2×

Produkt 1

HCID 459257414-(4-Amino-2,6-difluorophenyl)piperazine, N1-BOC protectedAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(2,6-difluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Intermediate II) (30 g, 0.09 mol), in methanol (500 mL) under argon atmosphere was added 10% Pd/C (4.5 g, 15 mol% by weight). Flask was evacuated and hydrogen was introduced with the help of balloon. The reaction mixture was stirred under hydrogen and progress of the reaction was monitored by TLC. On completion, the reaction mixture was filtered through celite pad using methanol as solvent. The filterate was evaporated to provide title compound (26 g, 95%) as pale yellow solid.

Aufarbeitung

  1. customFlask was evacuated
  2. additionhydrogen was introduced with the help of balloon
  3. filtrationOn completion, the reaction mixture was filtered through celite pad
  4. customThe filterate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f5e87f5aac9b41b1878c83a473639e46
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841306B2

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