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

HRID 734567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734567
[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][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)[N:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[CH3:20][CH:19]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[NH2:27])[CH2:18][N:15]1[CH2:14][CH2:13][N:12]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]3)[CH2:17][CH2:16]1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 574443342-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline

Produkt 1

HCID 574443353-{1-Methyl-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}anilineAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline (70 mg) in methanol (1 mL) was added dropwise to a stirred suspension of iron powder (3.0 equiv., 30 mg) and ammonium chloride (5.0 equiv., 48 mg) in water (1 mL). The reactants were heated at reflux for 18 hours. The reaction mixture was cooled to room temperature then filtered using a Millipore filter. The filtrate was concentrated under reduced pressure and purified using chromatography (SiO2, SPE) eluting with DCM-methanol (95:5) to afford the title compound (40 mg, 60% yield).

Aufarbeitung

  1. temperatureThe reactants were heated
  2. temperatureat reflux for 18 hours
  3. filtrationthen filtered
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified
  7. washeluting with DCM-methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-a801906fea21425c8a08029c3bbe5b9d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592346B2

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