Tetrahydrofuran → 1-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

HRID 74561

반응식

HRID 74561 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:39]CC1>>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:11]2[C:2]([Cl:1])=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][C:7]([O:12][CH3:13])=[CH:6][CH:5]=3)([OH:39])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 836472-Chloro-6-methoxyquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

생성물 1

HCID 581811261-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

반응 조건

온도
-78 °C

실험 절차

Under an argon atmosphere 5.0 g (25 mmol) 2-chloro-6-methoxyquinoline in a small amount of THF were added dropwise at −78° C. to 14 mL (28 mmol) of a 2 M lithium diisopropylamide solution (in THF) in 50 mL THF. Then the mixture was stirred for 1.5 h at −78° C. and 4.5 mL (25 mmol) N-benzylpiperidone was added dropwise. The mixture was stirred for a further 15 min with cooling before slowly being heated to RT. The reaction mixture was stirred overnight, evaporated down and purified by flash chromatography on aluminium oxide. The product-containing fractions were combined and evaporated down.

후처리

  1. stirringThe mixture was stirred for a further 15 min
  2. temperaturewith cooling
  3. temperaturebefore slowly being heated to RT
  4. stirringThe reaction mixture was stirred overnight
  5. customevaporated down
  6. custompurified by flash chromatography on aluminium oxide
  7. customevaporated down

출처 및 근거

ORD 기록
ord-9443c894840b43aa8c4008ecd5502c39
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829006B2

연결된 노트

불러오는 중…