1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-Chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine

HRID 1450191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1450191
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](Cl)=[N:10][C:4]=2[CH:3]=1.[CH2:18]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].N12CCCN=C1CCCCC2>C(#N)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([N:30]3[CH2:31][CH2:32][N:27]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:28][CH2:29]3)=[N:10][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27370981-NonylpiperazineHCID 189404158,11-Dichlorodibenzo[b,f][1,4]oxazepine

Produkt 1

HCID 99329128-Chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The mixture of 8, 11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The title compound was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationAfter the mixture was concentrated
  4. additionwater (20 mL) and ethyl acetate (20 mL) were added
  5. customThe two phases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×20 mL)
  7. dry with materialThe combined ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was then concentrated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2a86a5ccf062426180fdfd456bd589e3
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602121

Notizen zur Reaktion

Wird geladen…