Potassium Iodide → HCID 85873142, 화합물

HRID 748509노트

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HRID 748509 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 85873142HCID 85873142, 화합물수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c14b4ca0af4d41bb987c10e1fa7200e9
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399780B2

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