Water → (3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine

HRID 514279

Reaktionsgleichung

Reaktionsgleichung von HRID 514279
Br.[Br-].[CH3:3][NH:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH:32]1[C:42]2[C:41](=O)[C:40]3[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=3[CH2:38][O:37][C:36]=2[CH:35]=[CH:34][CH:33]=1.O>O1CCCC1.CCCCCCC>[CH3:3][NH:4][CH2:5][CH2:6]/[CH:7]=[C:41]1\[C:40]2[C:39]([CH2:38][O:37][C:36]3[C:42]\1=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:47][CH:46]=[CH:45][CH:44]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 78259Dibenz[b,e]oxepin-11(6H)-oneHCID 19897074[3-(Methylamino)propyl]triphenylphosphonium Bromide HydrobromideHCID 178418339Butyllithium

Produkt 1

HCID 6433351(3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

Desmethyldoxepin is prepared according to the following method. Anhydrous 3-methylaminopropyltriphenylphosphonium bromide hydrobromide (1530 g) prepared as in U.S. Pat. No. 3,509,175, is suspended in 4.5 L dry tetrahydrofuran and 6.0 moles of butyl lithium in heptane is added during 1 hour. After an additional 30 minutes, 483 g of 6,11-dihydrodibenz[b,e]oxepin-11-one, is added to the deep red solution and the reaction is maintained at reflux for 10 hours. Water, 500 mL, is added at room temperature and the solvent is removed in vacuo. The crude residue is treated with 10% hydrochloric acid until acidic (pH 2) and then 1.5 L benzene is added. After stiffing, the mixture separates into three phases (an insoluble hydrochloride salt product phase, an aqueous phase and an organic phase). The benzene layer is removed by decantation and the remaining mixture is rendered basic with 10% sodium hydroxide solution and is extracted with 3×1500 mL portions of benzene. The benzene extracts are washed, then dried with anhydrous sodium sulfate and concentrated in a vacuum leaving a solid residue of desmethyldoxepin.

Aufarbeitung

  1. customDesmethyldoxepin is prepared
  2. temperaturethe reaction is maintained
  3. temperatureat reflux for 10 hours
  4. customthe solvent is removed in vacuo
  5. additionThe crude residue is treated with 10% hydrochloric acid until acidic (pH 2)
  6. addition1.5 L benzene is added
  7. customThe benzene layer is removed by decantation
  8. extractionis extracted with 3×1500 mL portions of benzene
  9. washThe benzene extracts are washed
  10. dry with materialdried with anhydrous sodium sulfate
  11. concentrationconcentrated in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-13d50cfcbe76413d9a661c8e5a1aa9d9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107898B2

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