Water → 1'-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

HRID 419415노트

반응식

HRID 419415 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([Cl:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C([O-])([O-])=O.[K+].[K+].[N:20]1([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>CS(C)=O>[Cl:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:29]1[CH2:30][CH2:31][CH:26]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:27][CH2:28]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 786071,4'-BipiperidineHCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzene

생성물 1

HCID 594529741'-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-1,4'-bipiperidine수율 71%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

4-Chloro-5-fluoro-2-nitrophenyl methyl ether (2.19 g, 10.7 mmol) was dissolved in DMSO (10 mL). K2CO3 (2.2 g, 16 mmol) and 1,4′-bipiperidine (1.8 g, 11 mmol) were added and the reaction mixture was allowed to stir overnight at rt. The mixture was then poured into H2O and extracted with EtOAc (2×) and then the combined organics were extracted with H2O (5×). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo. The resulting residue was adsorbed onto silica gel and flash chromatographed to give the title compound of step C (2.69 g, 71%). MS (M+H, ES+) 354.

후처리

  1. extractionextracted with EtOAc (2×)
  2. extractionthe combined organics were extracted with H2O (5×)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed

출처 및 근거

ORD 기록
ord-5d416f9964cb4bb8b084e2c8c03b3c4f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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