3-Aminobenzonitrile → 1-(3-Cyanophenyl)piperazine

HRID 276894

Reaktionsgleichung

Reaktionsgleichung von HRID 276894
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl.Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl>C1(C)C(C)=CC=CC=1.[OH-].[Na+]>[C:5]([C:4]1[CH:3]=[C:2]([N:1]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Komponenten

5

Edukt 2

HCID 167023-AminobenzonitrileHCID 522769Bis(2-chloroethyl)amine hydrochloride

Produkt 1

HCID 114809021-(3-Cyanophenyl)piperazineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7237O-XyleneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

3-Aminobenzonitrile (6.1 g, 52 mmol) and bis(2-chloroethyl)amine hydrochloride (10 g, 57 mmol) were dissolved in xylene (100 ml), and the resulting solution was stirred at 150 to 160° C. for 5 hours. Supernatant fluid of the reaction solution was discarded, the remaining residue was dissolved in sodium hydroxide aqueous solution (1 N) and then the reaction product was extracted therefrom with ethyl acetate. The extract was washed with saturated brine, and then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 3.2 g of the title compound (17 mmol, 34% in yield). A portion of the thus obtained compound was made into hydrochloric acid salt by treating it with hydrochloric acid-saturated methanol.

Aufarbeitung

  1. extractionthe reaction product was extracted
  2. washThe extract was washed with saturated brine
  3. customthe compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16226fadb74f4ca2baebda3f682e8192
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355642B1

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