Ethanol → 4-(Piperidine-1-sulfonyl)aniline

HRID 1366824

Reaktionsgleichung

Reaktionsgleichung von HRID 1366824
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.NO>[Fe].O>[N:13]1([S:10]([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 787HydroxylamineHCID 25517Ammonium ChlorideHCID 7236241-[(4-Nitrophenyl)sulfonyl]piperidine

Produkt 1

HCID 2366484-(Piperidine-1-sulfonyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

1-(4-Nitro-benzenesulfonyl)-piperidine (30 g) was mixed with iron powder (50 g), ammonium chloride (50 g), ethanol (200 ml) and water (50 ml). The mixture was heated under reflux conditions for 2 h. LCMS showed that the reduction goes through a hydroxylamine intermediate. The mixture was filtered through Celite while hot and the iron residues washed with warm ethanol, ethyl acetate, water and dichloromethane. All volatiles were removed under reduced pressure and the residue partitioned between water and ethyl acetate. The organic solution was separated and washed with brine, dried over MgSO4 concentrated to give 4-(piperidine-1-sulfonyl)-phenylamine, 23 g. 1HNMR CDCl3 7.43 (2H, d), 6.67 (2H, d), 3.33 (2H, bs), 2.84 (4H, t), 1.53 (4H, m), 1.31 (2H, m)

Aufarbeitung

  1. temperatureThe mixture was heated under reflux conditions for 2 h
  2. filtrationThe mixture was filtered through Celite while hot and the iron residues
  3. washwashed with warm ethanol, ethyl acetate, water and dichloromethane
  4. customAll volatiles were removed under reduced pressure
  5. customthe residue partitioned between water and ethyl acetate
  6. customThe organic solution was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5e5f8a78e000446392525fde91d67ea5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893077B2

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