반응 #42978

반응 방정식

(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

용매

acetonitrile

water

반응 조건

후처리

1. 1
   온도warmed to 50° C.
2. 2
   workup.STIRRINGstirred 13 hours
3. 3
   온도The mixture was cooled to room temperature
4. 4
   기타acetonitrile was removed under reduced pressure
5. 5
   추출The aqueous layer was extracted with ethyl acetate (750 mL)
6. 6
   세척the extract was washed with brine
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The crude residue was purified by silica gel chromatography (3:1 ethyl acetate:hexanes)

실험 절차

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.

출처