反応 #42978

反応方程式

(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

溶媒

acetonitrile

water

反応条件

後処理

1. 1
   温度warmed to 50° C.
2. 2
   workup.STIRRINGstirred 13 hours
3. 3
   温度The mixture was cooled to room temperature
4. 4
   その他acetonitrile was removed under reduced pressure
5. 5
   抽出The aqueous layer was extracted with ethyl acetate (750 mL)
6. 6
   洗浄the extract was washed with brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated
10. 10
    その他The crude residue was purified by silica gel chromatography (3:1 ethyl acetate:hexanes)

実験手順

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.

出典