Sodium Hydroxide → 8-Cyano-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 881939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881939
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([C:19]#[N:20])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[C: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)#[N:20]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22292795HCID 22292795, Verbindung

Produkt 1

HCID 104659028-Cyano-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-cyano-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (10 mg, 0.032 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred 1 hour at 50 C. The product mixture was diluted with water (5 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (5 mL), dried with Na2SO4 and concentrated to give 6.0 mg of a white solid. 1H NMR (400 MHz, CD3OD) d 7.33 (s, 1H), 6.93 (s, 1H), 3.91 (s, 3H), 3.18-2.97 (m, 5H), 2.80 (m, 1H), 2.60 (m, 1H), 1.33 (d, J=8 Hz, 3H). MS calculated for C13H16N2O+H: 217, observed: 217.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9160a465c6244c3e95f695e631b5c923
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993750B2

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