Potassium Iodide → HCID 85873142, compound

HRID 748509Notes

Reaction equation

HRID 748509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N+:3]=1[O-:10].[CH3:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[I-].[K+].C(=O)([O-])[O-]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:15]2[CH2:16][CH2:17][CH:12]([CH3:11])[CH2:13][CH2:14]2)=[CH:4][N+:3]=1[O-:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 19660Carbonate IonHCID 693814-MethylpiperidineHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 85873142HCID 85873142, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine 1-oxide (222 mg, 1.25 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) in tetrahydrofuran (2 mL) were added a solution of 4-methylpiperidine (247 mg, 2.49 mmol) in tetrahydrofuran (1.5 mL), a catalytic amount of potassium iodide, and MP-Carbonate (2.55 mmol/g, 1.47 g, 3.74 mmol). The mixture was gently stirred at room temperature for one week. The mixture was filtered (20 μm polyethylene filter), and the beads were washed with several portions of methylene chloride. The filtrate was washed with NaHCO3 (aq. sat.), dried (Na2SO4), and the solvent was evaporated to give a crude product which was purified by column chromatography using chloroform/ethanol, (95:5), as the eluent to give 168 mg (56% yield) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.37 (d, J=1 Hz, 1 H), 7.41 (d, J=8 Hz, 1 H), 7.20 (dd, J=8, 2 Hz, 1 H), 3.41 (s, 2 H), 2.80-2.75 (m, 2 H), 2.00 (dt, J=12, 2 Hz, 2 H), 1.63-1.58 (m, 2 H), 1.45-1.30 (m, 1 H), 1.22 (m, 2 H), 0.92 (d, J=6 Hz, 3 H); MS (ES) m/z 241 (M++1).

Workup

  1. filtrationThe mixture was filtered
  2. filtration(20 μm polyethylene filter)
  3. washthe beads were washed with several portions of methylene chloride
  4. washThe filtrate was washed with NaHCO3 (aq. sat.)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated
  7. customto give a crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c14b4ca0af4d41bb987c10e1fa7200e9
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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