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

HRID 1689688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689688
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:21])[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[CH2:18]([O:17][C:15]1[C:14]([Cl:21])=[CH:13][C:9]2[CH:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:16]=1)[CH:19]=[CH2:20]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22292782N-trifluoroacetyl-7-allyloxy-8-chloro-1-methyl-2,3,4,5tetrahydro-1H-3-benzazepine

Produkt 1

HCID 104673597-Allyloxy-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineAusbeute 114,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of N-trifluoroacetyl-7-allyloxy-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (23 mg, 0.066 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred overnight at 20° 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 19 mg of a white solid. 1H NMR (400 MHz, CD3OD) δ 7.12 (s, 1H), 6.81 (s, 1H), 6.03 (m, 1H), 5.43 (d, J=17 Hz, 1H), 5.24 (d, J=10 Hz, 1H), 4.57 (d, J=5 Hz, 2H), 3.1-2.9 (m, 5 H), 2.81 (m, 1H), 2.63 (m, 1H), 1.30 (d, J=7 Hz, 3H).

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-0452daf030894069beaf23035a31b537
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153621B2

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