반응 #161738

반응 방정식

water

2-chloroquinoline

lithium diisopropylamide

N-benzylpiperidone

→

1-benzyl-4-(2-chloro-quinolin-3-yl)-piperidin-4-ol

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 40 min at −70° C. and for 3 h at RT
2. 2
   온도The reaction mixture was cooled to −20° C.
3. 3
   기타to come up to RT
4. 4
   추출extracted with EtOAc
5. 5
   기타The organic phase was dried
6. 6
   여과filtered
7. 7
   농축concentrated to dryness by rotary evaporation
8. 8
   기타The product was purified
9. 9
   농축concentrated to dryness by rotary evaporation

실험 절차

Under an argon atmosphere 22.3 g (136 mmol) 2-chloroquinoline in 60 mL THF was slowly added dropwise at −78° C. to 68.0 mL (136 mmol) of a 2M lithium diisopropylamide (in THF) solution in 280 mL THF. The reaction mixture was stirred for 1 h at −78° C. and then 24.3 mL (136 mmol) N-benzylpiperidone in 50 mL of THF were added dropwise. The reaction mixture was stirred for 40 min at −70° C. and for 3 h at RT. The reaction mixture was cooled to −20° C., and 200 mL water were added dropwise. The reaction mixture was allowed to come up to RT and extracted with EtOAc. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation. The product was purified using an Alox column. The product-containing fractions were combined and concentrated to dryness by rotary evaporation.

출처