Potassium Carbonate → HCID 66758680, Verbindung

HRID 1943975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943975
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH:26]=[C:27]1[C:33]2[CH:34]=[CH:35][CH:36]=[N:37][C:32]=2[CH2:31][O:30][C:29]2[CH:38]=[CH:39][C:40]([C:42](=[O:44])[CH3:43])=[CH:41][C:28]1=2>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][N:11]([CH2:24][CH2:25][CH:26]=[C:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[N:37][C:32]=4[CH2:31][O:30][C:29]4[CH:38]=[CH:39][C:40]([C:42](=[O:44])[CH3:43])=[CH:41][C:28]3=4)[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-olHCID 66758314HCID 66758314, Verbindung

Produkt 1

HCID 66758680HCID 66758680, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of the (S)-4-(4-chloro-phenyl)-3,3-dimethyl-piperidin-4-ol (5.50 g, 22.94 mmol) in acetonitrile (200 mL) and water (50 mL) was added potassium carbonate (7.17 g, 51.9 mmol) followed by solid 1-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-ethanone (6.30 g, 17.3 mmol). The heterogeneous mixture was stirred at room temperature 4 hours, warmed to 50° C. and stirred 13 hours. The mixture was cooled to room temperature and acetonitrile was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (750 mL) and the extract was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (3:1 ethyl acetate:hexanes) to afford (S)-1-(5-{3-[4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl)-ethanone as an off-white solid.

Aufarbeitung

  1. temperaturewarmed to 50° C.
  2. stirringstirred 13 hours
  3. temperatureThe mixture was cooled to room temperature
  4. customacetonitrile was removed under reduced pressure
  5. extractionThe aqueous layer was extracted with ethyl acetate (750 mL)
  6. washthe extract was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica gel chromatography (3:1 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cff28fc1465e4d9bb261810bc0e3edb2
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394817B2

Notizen zur Reaktion

Wird geladen…