Ammonium Chloride → 1-(2-piperidin-1-yl-ethyl)-1H-indazol-5-ylamine

HRID 1790119

Reaktionsgleichung

Reaktionsgleichung von HRID 1790119
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[N:8]=[CH:7]2)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:15]1([CH2:14][CH2:13][N:9]2[C:10]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:7]=[N:8]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 114927965-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole

Produkt 1

HCID 696527271-(2-piperidin-1-yl-ethyl)-1H-indazol-5-ylamineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole (4.3 g, 16 mmol), iron powder (8.8 g, 157 mmol), and ammonium chloride (430 mg, 8 mmol) in a 4:1 ethanol/H2O solution (75 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 50 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound (3.4 g, 93%). 1H NMR (300 MHz, DMSO-d6) ppm 1.34–1.45 (m, 6H), 2.36 (m, 4H), 2.64 (t, J=6.44, 2H), 4.35 (t, J=6.44, 2H), 4.76 (s, 2H), 6.71 (m, 1H), 6.79 (m, 11H), 7.35 (m, 1H), 7.67 (m, 1H); MS (DCI/NH3) m/z 245 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a1e8f338515341c5b9013f5d60ce2d31
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071182B2

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