Ammonium Chloride → 3-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

HRID 734492

Reaktionsgleichung

Reaktionsgleichung von HRID 734492
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)[CH2:14][CH2:13]2)[N:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[NH2:26])[CH2:16][CH2:17]2)[N:3]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium Chloride2×HCID 498519022-Methyl-5-(4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

Produkt 1

HCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}anilineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysator2×HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline (D5) (0.14 g; 1 eq) in methanol (3 mL) was added dropwise to a suspension of iron powder (0.07 g; 3.2 eq) and ammonium chloride (0.1 g; 5.3 eq) in water (3 mL). The reactants were heated at reflux for 8 hours, adding additional amounts of iron powder (total 0.07 g; 3.2 eq) and ammonium chloride (total 0.1 g; 5.03 eq) in 3 portions during the reaction. The reaction mixture was filtered using a Millipore filter. The filtrate was concentrated under reduced pressure, diluted with water (5 mL) and a saturated aqueous solution of sodium hydrogen carbonate (2 mL), extracted into ethyl acetate (3×5 mL), dried over Na2SO4 and concentrated under reduced pressure obtaining the title compound in 84% yield (0.11 g).

Aufarbeitung

  1. temperatureThe reactants were heated
  2. temperatureat reflux for 8 hours
  3. customduring the reaction
  4. filtrationThe reaction mixture was filtered
  5. filtrationfilter
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additiondiluted with water (5 mL)
  8. extractiona saturated aqueous solution of sodium hydrogen carbonate (2 mL), extracted into ethyl acetate (3×5 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9cc5eea985ac4dcfbc1442cd2f95c9c8
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592346B2

Verknüpfte Notizen

Wird geladen…