Sodium Carbonate → HCID 131717513、化合物

HRID 1885316ノート

反応式

HRID 1885316 の反応式
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][N:8]=1)=[O:6].[F:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[OH2:6].[ClH:1].[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[S:9][N:8]=3)=[O:6])[CH2:27][CH2:28]2)=[O:22])=[CH:29][CH:30]=1.[ClH:1]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2737266(4-Fluorophenyl)(piperidin-1-yl)methanoneHCID 10263700HCID 10263700、化合物

生成物 1

HCID 131717513HCID 131717513、化合物収率 27.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
180 °C

実験手順

A mixture of N-(2-chloroethyl)-1,2-benzisothiazole-3-carboxamide (3.5 g) and 1-(4-fluorobenzoyl)piperidine (3.63 g) in dry 1-methyl-2-pyrrolidinone (125 ml) was heated with stirring to 180° C., under nitrogen. After 3 hr, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium carbonate solution. The aqueous phase was extracted with ethyl acetate, and the combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was triturated with ether, and the filtrate was concentrated. The residue was chromatographed on silica using ethyl acetate as the eluent. The appropriate fractions were combined and concentrated. The residue was taken up in ether and hydrogen chloride in ether was added. The precipitate was recrystallized from methanol/dichloromethane/ether to provide 1.21 g (18.1%) of product, mp 188°-190° C.

後処理

  1. temperaturewas heated
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was triturated with ether
  9. concentrationthe filtrate was concentrated
  10. customThe residue was chromatographed on silica
  11. concentrationconcentrated
  12. additionhydrogen chloride in ether was added
  13. customThe precipitate was recrystallized from methanol/dichloromethane/ether

出典と根拠

ORDレコード
ord-2df9d57137dd44eab1c9230f2d870c32
出典データセット
uspto-grants-1992_09
特許番号
US05143923

反応ノート

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