Chlorosulfonic acid → HCID 22676671、化合物

HRID 412918ノート

反応式

HRID 412918 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].[Cl:20][S:21](O)(=[O:23])=[O:22]>ClCCl>[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:21]([Cl:20])(=[O:23])=[O:22])=[CH:16][CH:17]=2)[CH2:7][CH2:6]1)=[O:4]

参加物

4

反応物 2

HCID 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 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 1-(trifluoroacetyl)-4-benzylpiperidine (29.2 g, 108 mmol) and dichloromethane (10 ml) was added dropwise to chlorosulfonic acid (36 ml, 539 mmol) over period of 1 h at −10° C. The mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The whole was poured into ice-water (500 ml). The mixture was extracted with dichloromethane (200 ml×2). The extracts were washed with 5% aqueous sodium bicarbonate (500 ml), saturated sodium chloride solution (500 ml) successively. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20 to 1/5) to obtain the title compound (16.5 g, 41%) as a colorless crystalline powder.

後処理

  1. waitat room temperature for 1 h
  2. extractionThe mixture was extracted with dichloromethane (200 ml×2)
  3. washThe extracts were washed with 5% aqueous sodium bicarbonate (500 ml), saturated sodium chloride solution (500 ml) successively
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel 100 g, ethyl acetate/hexane=1/20 to 1/5)

出典と根拠

ORDレコード
ord-74355547d2874b488d7c770ee7c91b8f
出典データセット
uspto-grants-2003_05
特許番号
US06562978B1

反応ノート

読み込み中…