Sodium Carbonate → 1-{[3-(Chloromethyl)phenyl]sulfonyl}piperidine

HRID 1967558ノート

反応式

HRID 1967558 の反応式
P(Cl)(Cl)([Cl:3])=O.[N:6]1([S:12]([C:15]2[CH:16]=[C:17]([CH2:21]O)[CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:3][CH2:21][C:17]1[CH:16]=[C:15]([S:12]([N:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanol

生成物 1

HCID 657454631-{[3-(Chloromethyl)phenyl]sulfonyl}piperidine収率 59%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

Phosphorus oxychloride (1.00 mL) was added to DMF (5.0 mL), and stirred at 80° C. for 30 minutes. A solution prepared by dissolving [3-(piperidin-1-ylsulfonyl)phenyl]methanol (2.00 g) obtained in Reference Example 21 in DMF (5.0 mL) was added to it, and stirred at 80° C. for 30 minutes. At 0° C., aqueous saturated sodium carbonate solution was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient) to give the entitled compound (1.26 g, 59%) as a colorless solid.

後処理

  1. customA solution prepared
  2. additionwas added to it
  3. stirringstirred at 80° C. for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine in that order
  6. dry with materialdried with sodium sulfate
  7. customThe drying agent was removed through filtration
  8. customthe solvent was evaporated off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient)

出典と根拠

ORDレコード
ord-944b10a56b32427ca3664bb1a5e99fd7
出典データセット
uspto-grants-2013_04
特許番号
US08420823B2

反応ノート

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