Piperazine → 2-Piperazin-1-yl-quinazoline

HRID 1276596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1276596
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[N:11][C:2]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 740542-Chloroquinazoline

Produkt 1

HCID 64232662-Piperazin-1-yl-quinazolineAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-chloroquinazoline (5 g) in 20 mL of toluene is added dropwise to a refluxing solution of piperazine (20 g) in 150 mL of toluene. The solution is heated for an additional 24 hours. After cooling to 0° C. for about 30 minutes, the solution is filtered. The filtrate is extracted with 10% acetic acid. The aqueous extracts are washed with ether, basified and extracted with toluene. The toluene layer is then washed with water, dried and concentrated. The resulting material is placed under vacuum overnight to afford the title compound (6.8 g, m.p. 64-66° C.). 1H NMR (CDCl3) 9.0 (s, 1H) , 7.66 (m, 2H), 7.56 (d, J=8 Hz, 1H), 7.22 (ddd, J=8,7,1 Hz, 1H), 4.0 (t, J=5 Hz, 4H), 3.05 (t, J=5 Hz, 4H).

Aufarbeitung

  1. temperatureThe solution is heated for an additional 24 hours
  2. filtrationthe solution is filtered
  3. extractionThe filtrate is extracted with 10% acetic acid
  4. washThe aqueous extracts are washed with ether
  5. extractionextracted with toluene
  6. washThe toluene layer is then washed with water
  7. customdried
  8. concentrationconcentrated
  9. customis placed under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-ef54229253a44451904777eac1b9c5d5
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166205

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