Chloroacetamide → 2-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamide

HRID 346452

Reaktionsgleichung

Reaktionsgleichung von HRID 346452
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:10]=2[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]([NH2:32])=[O:31]>CC(C)=O>[F:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[CH2:12][CH2:13][N:14]([CH2:29][C:30]([NH2:32])=[O:31])[CH2:15][CH2:16][C:10]=2[CH:9]=1

Komponenten

5

Edukt 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 210801847-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride

Produkt 1

HCID 114616002-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 70 mg (0.23 mmol) of 7-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [Example 1c)] in 1 ml of acetone was successively treated with 69 mg (0.5 mmol) of potassium carbonate and 24 mg (0.25 mmol) of 2-chloroacetamide. The reaction mixture was heated to reflux during 18 h. For the working-up, 1 g of silica gel was added to the cooled reaction mixture, which was then evaporated under reduced pressure. For purification, the crude material obtained was chromatographed on silica gel using a 95:5:0.1-mixture of dichloromethane, methanol and ammonium hydroxide as the eluent. There were obtained 38 mg (51% of theory) of 2-[7-(3-fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamide as a white solid; MS: m/e 329 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux during 18 h
  3. addition1 g of silica gel was added to the cooled reaction mixture, which
  4. customwas then evaporated under reduced pressure
  5. customFor purification
  6. customthe crude material obtained
  7. customwas chromatographed on silica gel using a 95:5

Quellen und Nachweise

ORD-Eintrag
ord-108d1cfb19e5400cb33f1a87da97a5a0
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173023B2

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