Potassium Iodide → 3-Cyclobutyl-7-(2,4-difluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 222682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222682
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:14]=3[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1.[F:23][C:24]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:25]=1[CH2:26]Br.[I-].[K+]>CC(=O)CC>[CH:7]1([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([O:22][CH2:26][C:25]4[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:24]=4[F:23])[CH:20]=[CH:21][C:14]=3[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Produkt 1

HCID 104051733-Cyclobutyl-7-(2,4-difluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

Potassium carbonate (778 mg, 5.6 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (868 mg, 4.0 mmol), 2,4-difluorobenzyl bromide (0.25 ml, 2.1 mmol) and potassium iodide (25 mg) in butanone (9 ml). The reaction mixture was stirred at reflux for 18 hours, cooled, filtered and concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 then 1:9:10) afforded the title compound (E79); MS (ES+) m/e 344 [M+H]+.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification of the resulting residue by column chromatography
  11. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5

Quellen und Nachweise

ORD-Eintrag
ord-9ae2475e8387403f8c46c5e812725c23
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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