3,5-Dichlorobenzenesulfonyl chloride → 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole

HRID 1006417

反応式

HRID 1006417 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[C:28]([Cl:30])[CH:29]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+].O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:31]([C:26]2[CH:25]=[C:24]([Cl:23])[CH:29]=[C:28]([Cl:30])[CH:27]=2)(=[O:33])=[O:32])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 27285324-(4-Benzyl-piperazin-1-yl)-1H-indole

生成物 1

HCID 121371244-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole収率 100.5%

試薬・触媒・溶媒 4

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

4-(4-Benzyl-piperazin-1-yl)-1H-indole (274 mg, 0.94 mmole) and 50 mg tetra-n-butylammonium hydrogen sulfate was stirred in a mixture of 10 mL toluene and 5 mL 4 N sodium hydroxide. Solid 3,5-dichlorobenzenesulfonyl chloride (246 mg, 1.0 mmole) was added in one portion. The reaction mixture was stirred at room temperature for 6 hours, then it was diluted with 20 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 10 mL saturated sodium chloride solution, dried (magnesium sulfate) and concentrated. Recrystallization from dichloromethane provided 473 mg of 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole, m.p. 201-203° C.

後処理

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 10 mL saturated sodium chloride solution
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customRecrystallization from dichloromethane

出典と根拠

ORDレコード
ord-9c0ec165595848a990ab93ee514ccaec
出典データセット
uspto-grants-2004_09
特許番号
US06790848B2

関連ノート

読み込み中…