Sodium hydride → 11-[4-(2-Cyanobenzyl)-1-piperazinyl]dibenz[b,f][1,4]oxazepine

HRID 1450184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1450184
[N:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:25][C:26]1[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=1>CN(C=O)C>[C:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]=2)[CH2:6][CH2:5]1)#[N:33]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 706187411-(Piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine

Produkt 1

HCID 1897134211-[4-(2-Cyanobenzyl)-1-piperazinyl]dibenz[b,f][1,4]oxazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine (2.79 g, 10.0 mmol) (prepared from 10,11-dihydrodebenz[b,f][1,4]oxazepine-11-one, Aldrich and piperazine, as in example 1) in DMF (25 mL) was added sodium hydride (0.56 g, 60% in oil, 14 mmol) at 0° C. under argon. The mixture was stirred at 0° C. for 10 minutes at room temperature for 20 minutes, and then treated with α-bromo-o-tolunitrile (2.35 g, 12.0 mmol, Aldrich). The resulting mixture was stirred at room temperature overnight and quenched with saturated ammonium chloride solution (25 mL). The mixture was separated and extracted with ethyl acetate (3×50 mL). The combined organic phase was dried over magnesium sulfate and filtered. The filtrate was 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 (2.34 g, 59%), m.p. 136°-138° C.; MS 395 (M+ +1).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customquenched with saturated ammonium chloride solution (25 mL)
  3. customThe mixture was separated
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f0875813a71c4db8a298e0f89d0c3e74
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602120

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