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Water → 11-Cyano-11-[2-(Dimethylamino)ethyl]-6,11-dihydrodibenz[b,e]oxepin

HRID 1156277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1156277
[H-].[Na+].[C:3]([CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)#[N:4].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl.O>CN(C)C=O>[C:3]([C:5]1([CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)#[N:4]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 12962149HCID 12962149, Verbindung

Produkt 1

HCID 1296215711-Cyano-11-[2-(Dimethylamino)ethyl]-6,11-dihydrodibenz[b,e]oxepinAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

Sodium hydride (5.0 g; 0.10 mole) is added portionwise with cooling (5°-10° C.) under a nitrogen atmosphere to a solution of 11-cyano-6,11-dihydrodibenz[b,e]oxepin of Example 1A, (20.0 g; 0.09 mole) in dry DMF (200 ml). After thirty minutes, effervescence ceases and 2-dimethylaminoethyl chloride (10.0 g; 0.09 mole) in dimethyl formamide [DMF] (200 ml) is added dropwise. Stirring is continued at 80° C. for sixteen hours. The reaction is cooled and poured into three liters of water. After extraction with ether, the ether is re-extracted with 1 N HCl, and the combined aqueous extracts are made basic with 50% NaOH. After extracting with ether and drying (K2CO3), the solvent is removed in vacuo to provide an oil which is chromatographed on an alumina column. The resulting oil crystallizes upon standing and trituration with hexane yields 11.0 g (42%) of a solid of 11-cyano-11-[2-(dimethylamino)ethyl]-6,11-dihydrodibenz[ b,e]oxepin (m.p. 63°-65° C.),

Aufarbeitung

  1. waitAfter thirty minutes
  2. waitis continued at 80° C. for sixteen hours
  3. temperatureThe reaction is cooled
  4. extractionAfter extraction with ether
  5. extractionthe ether is re-extracted with 1 N HCl
  6. extractionAfter extracting with ether
  7. dry with materialdrying (K2CO3)
  8. customthe solvent is removed in vacuo
  9. customto provide an oil which
  10. customis chromatographed on an alumina column
  11. customThe resulting oil crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-5015e82ccd70483bbf730a54e4691a85
Quelldatensatz
uspto-grants-1982_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04335122

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