Dimethylformamide → HCID 18971342, Verbindung

HRID 2395234

Reaktionsgleichung

Reaktionsgleichung von HRID 2395234
Cl[C:2]1[CH:29]=[CH:28][C:5]2[O:6][C:7]3[CH:27]=[CH:26][CH:25]=[CH:24][C:8]=3[C:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:13][CH2:12]3)=[N:10][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:32][N:33](C=O)C>>[C:32]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([C:9]2[C:8]3[CH:24]=[CH:25][CH:26]=[CH:27][C:7]=3[O:6][C:5]3[CH:28]=[CH:29][CH:2]=[CH:3][C:4]=3[N:10]=2)[CH2:16][CH2:15]1)#[N:33]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 98874518-Chloro-11-(4-benzyl-1-piperazinyl)-dibenz[b,f][1,4]oxazepine

Produkt 1

HCID 18971342HCID 18971342, Verbindung

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 β-bromo-ο-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-84c079150d374caeb084e5422e57e433
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05814628

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