Cyclohexylmethyl-(2-nitro-4-phenoxy-phenyl)-amine → N1-cyclohexylmethyl-4-phenoxy-benzene-1,2-diamine

HRID 1241939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241939
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][C:10]=2[N+:22]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C1COCC1.[Pd]>[CH:1]1([CH2:7][NH:8][C:9]2[C:10]([NH2:22])=[CH:11][C:12]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 2

HCID 21937664Cyclohexylmethyl-(2-nitro-4-phenoxy-phenyl)-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 21061671N1-cyclohexylmethyl-4-phenoxy-benzene-1,2-diamineAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of cyclohexylmethyl-(2-nitro-4-phenoxy-phenyl)-amine (0.55 g, 1.69 mmol) in THF (50 mL) was added palladium, 10% on activated carbon (0.55 g). The reaction flask was equipped with a septum and was placed under vacuum for 3 min. This flask was placed under hydrogen atmosphere (balloon inflated with hydrogen) and the reaction mixture was stirred for 18 h. The palladium was filtered off through a plug of diatomaceous earth and washed with EtOAc. The solvent was removed via rotary evaporation providing N1-cyclohexylmethyl-4-phenoxy-benzene-1,2-diamine (0.50 g, 99% yield) which was used in the next step without further purification.

Aufarbeitung

  1. customThe reaction flask was equipped with a septum
  2. customThis flask was placed under hydrogen atmosphere
  3. filtrationThe palladium was filtered off through a plug of diatomaceous earth
  4. washwashed with EtOAc
  5. customThe solvent was removed via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e52b0719cf2a47ea87468d663bf92c3b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115644B2

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