Hydrogen Peroxide → 4-(4-Carbamoylpiperidin-1-yl)-3,5-dichloropyridine 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:23]>C(Cl)Cl>[C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:6]([Cl:17])=[CH:5][N+:4]([O-:23])=[CH:3][C:2]=2[Cl:1])[CH2:9][CH2:10]1)(=[O:15])[NH2:16]Participants
Procedure
To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (100 mg, 0.36 mmol) and hydrogen peroxide.urea complex (72 mg, 0.77 mmol) in CH2Cl2 (2 mL) cooled to 0° C. was added trifluoroacetic anhydride (0.10 mL, 0.73 mmol). After 30 min the solution was warmed to r.t., after a further 16 hours a saturated solution of Na2S2O5 (10 mL) was added. The mixture was extracted with CH2Cl2 (2×20 mL), the combined organic extracts were washed with a saturated solution of NaHCO3 (20 mL), brine (20 mL), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 98:2) to furnish the title compound as a white solid (20 mg, 19%), m.p. 130-133° C.; umax (CHCl3)/cm−1 3026. 2855, 1724, 1452, 1273, 1107.
Workup
- additionwas added
- extractionThe mixture was extracted with CH2Cl2 (2×20 mL)
- washthe combined organic extracts were washed with a saturated solution of NaHCO3 (20 mL), brine (20 mL)
- dry with materialdried (MgSO4)
- customthe solvent removed under reduced pressure
- customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 98:2)
Sources & evidence
- ORD record
- ord-5298882746d64db4b71669ad29bddfea
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778925B2
Reaction notes
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