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Acetic Acid → Tert-butyl 4-(4-amino-3-fluorophenyl)piperazine-1-carboxylate

HRID 1503838
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1503838
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O)(=O)C>[Zn].O1CCCC1.CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[CH:3][C:2]=1[F:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 66738172Tert-butyl 4-(3-fluoro-4-nitrophenyl)piperazine-1-carboxylate

Produkt 1

HCID 57652076Tert-butyl 4-(4-amino-3-fluorophenyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 28A (1.6 g, 4.9 mmol), zinc dust (3.2 g, 49 mmol) and acetic acid (5.4 mL) in 1/1 tetrahydrofuran/methanol (100 mL) was stirred at ambient temperature for 1 hour. The mixture was filtered and the filtrate was diluted with water and adjusted to pH 9. The mixture was extracted with ethyl acetate and the combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 99/1 dichloromethane/methanol to give the title compound. MS: 296 (M+H+).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  9. washeluting with 99/1 dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-f86f30308d844574881c63cbdf09ac61
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09212192B2

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