Water → 1-Benzyl-4-(2-chloroquinolin-3-yl)piperidin-4-ol

HRID 74556

반응식

HRID 74556 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:20]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH2:34]>C1COCC1>[CH2:20]([N:27]1[CH2:32][CH2:31][C:30]([C:11]2[C:2]([Cl:1])=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)([OH:34])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 119282-ChloroquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

생성물 1

HCID 184442481-Benzyl-4-(2-chloroquinolin-3-yl)piperidin-4-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

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.

후처리

  1. stirringThe reaction mixture was stirred for 40 min at −70° C. and for 3 h at RT
  2. temperatureThe reaction mixture was cooled to −20° C.
  3. customto come up to RT
  4. extractionextracted with EtOAc
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness by rotary evaporation
  8. customThe product was purified
  9. concentrationconcentrated to dryness by rotary evaporation

출처 및 근거

ORD 기록
ord-7ad3bc61e8654529b20e12021a07e38b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829006B2

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