Sodium Hydroxide → 2H-benzazepine

HRID 1630694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1630694
N1([C:7]2[CH:17]=[CH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][NH:15][C:9]=3[CH:8]=2)CCOCC1.[OH-].[Na+]>CO>[N:15]1[CH2:14][CH:13]=[CH:12][CH:11]=[C:10]2[CH:16]=[CH:17][CH:7]=[CH:8][C:9]=12

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 669638998-Morpholinobenzazepine

Produkt 1

HCID 866101862H-benzazepineAusbeute 192,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the N-acetyl benzazepine (0.14 g, 0.40 mmol) from step I above in methanol (10 mL) was added an aqueous 2 N solution of sodium hydroxide (10 mL). The reaction solution was heated under reflux for 72 hours and then cooled to room temperature. The resultant reaction mixture was extracted with dichloromethane, washed with water and aqueous saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue obtained was purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide) to give the desired 2H-benzazepine (0.11 g, 89%) as a white foam: 1H NMR (DMSO-d6, 500 MHz) δ 7.35 (t, J=7.5 Hz, 2H), 7.24 (t, J=7.5 Hz, 1H), 7.14 (d, J=7.5 Hz, 2H), 6.84 (d, J=2.5 Hz, 1H), 6.65-6.60 (m, 1H), 6.49-6.38 (br, 1H), 4.33 (d, J=8.5 Hz, 1H), 3.95 (d, J=14.5 Hz, 1H), 3.77 (d, J=14.5 Hz, 1H), 3.71 (t, J=5.0 Hz, 4H), 3.10-2.87 (m, 6H), 2.21-2.12 (m, 1H), 2.03-1.85 (m, 1H).

Aufarbeitung

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 72 hours
  3. customThe resultant reaction mixture
  4. extractionwas extracted with dichloromethane
  5. washwashed with water and aqueous saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash column chromatography (dichloromethane to 90:9:1 dichloromethane/methanol/concentrated ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-7daef4bb550140deab6f4536170e54c7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791101B2

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