Methyl iodide → 2-(1-Methylpiperidin-3-yl)-5-(trifluoromethyl)benzenamine

HRID 502732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502732
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)([O-])=O.I[CH3:21]>CC(C)=O.C1C=CC=CC=1.CO.[Pt](=O)=O>[CH3:21][N:16]1[CH2:17][CH2:18][CH2:19][CH:14]([C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=2[NH2:1])[CH2:15]1

Komponenten

7

Edukt 2

HCID 6328Methyl iodideHCID 463167623-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

Produkt 1

HCID 587119192-(1-Methylpiperidin-3-yl)-5-(trifluoromethyl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 345198Adams' catalystKatalysatorHCID 180AcetoneLösungsmittelHCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To an orange solution of 3-(2-nitro-4-(trifluoromethyl)phenyl)pyridine (1.4 g, 5.2 mmol) in 2 ml acetone and 1 mL benzene was added iodomethane (1.0 ml, 16 mmol). The solution was allowed to stand for 5 days, and was concentrated in vacuo to give an orange solid. A portion of this material was treated with platinum (IV) oxide (0.11 g, 0.49 mmol) in 5 ml MeOH under an atmosphere of hydrogen for approximately 24 h. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Purification by silica gel chromatography (MC/MeOH/conc. NH4OH) provided the title compound. MS (m/z): 259.0 (M+H)+. Calc'd for C13H17F3N2: 258.28.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customto give an orange solid
  3. customThe reaction was flushed with nitrogen
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (MC/MeOH/conc. NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-dda1087bd25d4938b7af3b541eb56ea4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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