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

HRID 221238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221238
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:19])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Cl:19][C:14]1[C:15]([O:17][CH3:18])=[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 22292769HCID 22292769, Verbindung

Produkt 1

HCID 100366298-Chloro-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineAusbeute 109,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-chloro7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.399 g, 1.24 mmol) in methanol (20 mL) was treated with 15% aqueous NaOH (20 mL), and stirred overnight at 20 C. The product mixture was diluted with water (100 mL), extracted twice with EtOAc (100 mL), the combined organic phases were washed with brine (100 mL), dried with Na2SO4 and concentrated to give 0.306 g of a yellow solid. 1H NMR (400 MHz, CDCl3) d 7.05 (s, 1 H), 6.59 (s, 1 H), 3.80 (s, 3 H), 3.0-2.8 (m, 6 H), 2.62 (m, 1 H), 2.16 (bs, 1 H), 1.24 (d, J=7 Hz, 3 H). MS calculated for C12H16ClNO+H: 226, observed: 226.

Aufarbeitung

  1. extractionextracted twice with EtOAc (100 mL)
  2. washthe combined organic phases were washed with brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f9005ff0c60e4219a576ea353466d837
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207158B2

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