3-[[4-(4-Nitrophenyl)-1-piperazinyl]methyl]benzonitrile → 4-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamine

HRID 1267112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267112
[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]>CCO.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]

Komponenten

4

Edukt 1

HCID 85908193-[[4-(4-Nitrophenyl)-1-piperazinyl]methyl]benzonitrile

Produkt 1

HCID 111854474-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamineAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred solution of 1-(3-cyano-benzyl)-4-(4-nitro-phenyl)-piperazine (52 g) in EtOH (1.2 L) and THF (300 mL) was added portionwise SnC2.2H2O (145.6 g) at room temperature and the mixture was heated at 55° C. for 16 hours. After evaporation of the solvents, the residue was taken in water, basified with NaOH at pH 14 and extracted with CH2Cl2. The organic layer was then washed with water, dried over Na2SO4, and evaporated. The residue was cristallized from disopropyl ether to give the title compound (40.5 g) as pale yellow crystals.

Aufarbeitung

  1. customAfter evaporation of the solvents
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was then washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ac384ac2747045f3a8ff3879b7ffcecf
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552022B1

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