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

HRID 473720Notes

Reaction equation

HRID 473720 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8bf9f7d05df64010be81b941982b3c5e
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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