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

HRID 473720ノート

反応式

HRID 473720 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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. MS (ESI, pos. ion) m/z: 223.1 (M+1).

後処理

  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

出典と根拠

ORDレコード
ord-8bf9f7d05df64010be81b941982b3c5e
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

反応ノート

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