Ammonium Chloride → 4-(Piperidin-1-yl)aniline

HRID 1665637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665637
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Fe]>[N:12]1([C:9]2[CH:8]=[CH:7][C:6]([NH2:3])=[CH:11][CH:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 81049Piperidine, 1-(4-nitrophenyl)-

Produkt 1

HCID 4135014-(Piperidin-1-yl)anilineAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Ammonium chloride (228 mg, 4.2 mmol) in water (4 mL) was added to a solution of 1-(4-nitro-phenyl)-piperidine (220 mg, 1.0 mmol) in THF (6 mL) and the resulting mixture was stirred at 75° C. for 30 minutes. Iron powder (238 mg, 4.2 mmol) was then added portion wise and the mixture stirred for 5 hours at 75° C. The reaction mixture was filtered over celite, the filtrate was basified with sodium bicarbonate solution and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 180 mg (96%) of 4-Piperidin-1-yl-phenylamine. LCMS: 177.13 (M+1)+, 80.6%, 1H NMR: (DMSO-d6): δ 6.67 (m, 2H), 6.47 (m, 2H), 4.51 (s, 2H), 2.57 (t, 4H), 1.6 (q, 4H), 1.49 (m, 2H)

Aufarbeitung

  1. stirringthe mixture stirred for 5 hours at 75° C
  2. filtrationThe reaction mixture was filtered over celite
  3. extractionthe product extracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d627c5649ddf43488284ccc7edd431d2
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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