Dichloromethane → 1-(3-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanone

HRID 1880146노트

반응식

HRID 1880146 반응식
Cl.Cl.[F:3][C:4]1[C:9]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:8][CH:7]=[CH:6][N:5]=1.C(Cl)Cl.C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O>[F:3][C:4]1[C:9]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:26](=[O:28])[CH3:27])[CH2:11]2)=[CH:8][CH:7]=[CH:6][N:5]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 674169432-Fluoro-3-(piperidin-3-yl)pyridine dihydrochloride

생성물 1

HCID 593268021-(3-(2-Fluoropyridin-3-yl)piperidin-1-yl)ethanone수율 18.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an ice cooled solution of 2-fluoro-3-(piperidin-3-yl)pyridine dihydrochloride (612 mg, 2.418 mmol), DCM (20 mL) and triethylamine (2022 μL, 14.51 mmol) was added acetic anhydride (229 μL, 2.418 mmol) dropwise. After 1 hour, the reaction was poured into water and the aqueous mixture back extracted once with DCM (10 mL). The combined organics were washed with 0.5M NaOH and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 0% to 100% EtOAc in hexane, to provide 1-(3-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone (100 mg, 0.450 mmol) as a light yellow syrup. [M+1]=223.1.

후처리

  1. extractionthe aqueous mixture back extracted once with DCM (10 mL)
  2. washThe combined organics were washed with 0.5M NaOH
  3. concentrationconcentrated in vacuo
  4. customchromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  5. washeluting with 0% to 100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-edf338f0215f465cabe36c791e200f76
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318718B2

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