Reaktion #42978

Reaktionsgleichung

(S)-4-(4-chloro-phenyl)-3,3-dimethyl-piperidin-4-ol

potassium carbonate

1-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-ethanone

→

(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

Lösungsmittel

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to 50° C.
2. 2
   workup.STIRRINGstirred 13 hours
3. 3
   TemperaturThe mixture was cooled to room temperature
4. 4
   Sonstigeacetonitrile was removed under reduced pressure
5. 5
   ExtraktionThe aqueous layer was extracted with ethyl acetate (750 mL)
6. 6
   Waschenthe extract was washed with brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe crude residue was purified by silica gel chromatography (3:1 ethyl acetate:hexanes)

Vorschrift

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.

Quelle