Dichloromethane → HCID 22676671、化合物

HRID 1006376ノート

反応式

HRID 1006376 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].C(Cl)Cl.[Cl:23][S:24](O)(=[O:26])=[O:25]>O>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([S:24]([Cl:23])(=[O:26])=[O:25])=[CH:16][CH:17]=2)[CH2:7][CH2:6]1)=[O:4]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 8977951-(4-Benzylpiperidin-1-yl)-2,2,2-trifluoroethanone

生成物 1

HCID 22676671HCID 22676671、化合物収率 41.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To the mixture of 1-(trifluoroacetyl)-4-benzylpiperidine (29.2 g, 108 mmol) and methylene chloride (10 ml) was dropwise added chlorosulfonic acid (36 ml, 539 mmol) at −10° C. for an hour. The mixture was stirred at 0° C. for an hour and then stirred at room temperature for an hour. The reaction mixture was poured into ice-cooled water (500 ml) and extracted with methylene chloride (200 ml×2). The extract was washed with an aqueous solution of 5% sodium bicarbonate (500 ml) and saturated brine (500 ml) successively. The organic phase was dried over magnesium sulfate (anhydrous), then concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20→1/5) to give the title compound as a colorless powdery crystal (16.5 g, 41%).

後処理

  1. customat −10° C.
  2. customfor an hour
  3. stirringstirred at room temperature for an hour
  4. additionThe reaction mixture was poured into ice-
  5. extractionextracted with methylene chloride (200 ml×2)
  6. washThe extract was washed with an aqueous solution of 5% sodium bicarbonate (500 ml) and saturated brine (500 ml) successively
  7. dry with materialThe organic phase was dried over magnesium sulfate (anhydrous)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20→1/5)

出典と根拠

ORDレコード
ord-e6674d20524c4cbb8a87b964372fe417
出典データセット
uspto-grants-2004_09
特許番号
US06787650B1

反応ノート

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