Potassium Iodide → HCID 85873142、化合物

HRID 748509ノート

反応式

HRID 748509 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 85873142HCID 85873142、化合物収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c14b4ca0af4d41bb987c10e1fa7200e9
出典データセット
uspto-grants-2008_07
特許番号
US07399780B2

反応ノート

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