1-[1-(2-Chloro-4-nitrophenyl)piperidin-4-yl]-1,4-dihydro-2h-3,1-benzoxazin-2-one → 1-[1-(4-Amino-2-chlorophenyl)piperidin-4-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 2414319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414319
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][O:19][C:18]2=[O:27])[CH2:13][CH2:12]1>C(O)(=O)C.O1CCCC1.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[CH2:20][O:19][C:18]3=[O:27])[CH2:15][CH2:16]2)=[C:2]([Cl:1])[CH:7]=1

Komponenten

5

Edukt 1

HCID 226445721-[1-(2-Chloro-4-nitrophenyl)piperidin-4-yl]-1,4-dihydro-2h-3,1-benzoxazin-2-one

Produkt 1

HCID 226446801-[1-(4-Amino-2-chlorophenyl)piperidin-4-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Iron powder (1.5 g) was added to a solution of the product from step (i) (1.37 g) in acetic acid (50 ml) and tetrahydrofuran (20 ml). After stirring at room temperature for 5 h, the mixture was filtered through celite, the solvent removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution. The organic layer was washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 50% ethyl acetate/isohexane. Yield 1.05 g.

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. customthe solvent removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customPurification
  8. washeluting with 50% ethyl acetate/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-7ada653c34424853b26131f5dcd74ffb
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06812226B2

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