Sodium Hydroxide → 8-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1035344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035344
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Br:21][C:14]1[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22292803N-Trifluoroacetyl-8-bromo-7-isopropoxy-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Produkt 1

HCID 100175568-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.014 g, 0.035 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred overnight at 20 C. The product mixture was diluted with water (3 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (3 mL), dried with Na2SO4 and concentrated to give 0.008 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.24 (s, 1 H), 6.64 (s, 1 H), 4.48 (m, 1 H), 2.98 (m, 3 H), 2.87 (m, 3 H), 1.36 (m, 6 H), 1.30 (d, J=7 Hz, 3 H). MS calculated for C14H20BrNO+H: 298, observed: 298.

Aufarbeitung

  1. extractionextracted twice with EtOAc (5 mL)
  2. washthe combined organic phases were washed with brine (3 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0f075694b3dc43bfa36800641623fdd3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546379B2

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