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

HRID 221270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221270
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([O:19][CH3:20])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>[Cl-].[Na+].O>[Br:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]=2[CH:15]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22292805N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Produkt 1

HCID 103799108-Bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineAusbeute 1.117,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.013 g, 0.03 mmol) methanol (0.5 mL) was treated with 15% aqueous NaOH (0.5 mL), and stirred overnight at 20 C. The product mixture was diluted with brine (5 mL), extracted twice with EtOAc (5 mL), dried with MgSO4, and concentrated to give 0.10 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.08 (s, 1 H), 6.64 (s, 1 H), 3.72 (s, 3 H), 3.2-3.10 (m, 3 H), 2.7-2.5 (m, 3 H), 2.3-2.1 (m, 2 H), 0.96 (d, 3 H), 0.63 (d, 3 H). MS calculated for C14H20BrNO+H: 298, observed: 298.

Aufarbeitung

  1. extractionextracted twice with EtOAc (5 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e7a277fc95e141ec87cd52812e81ba9e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207158B2

Notizen zur Reaktion

Wird geladen…