Benzenesulfonyl chloride → t-butyl 4-(1-benzenesulfonyl-1H-indol-4-yl)piperazine-1-carboxylate

HRID 1006420

반응식

HRID 1006420 반응식
[C:1]([O:5][C:6]([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)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1.O>[C:1]([O:5][C:6]([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:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 22015386tert-Butyl 4-(1H-indol-4-yl)piperazine-1-carboxylate

생성물 1

HCID 22015366t-butyl 4-(1-benzenesulfonyl-1H-indol-4-yl)piperazine-1-carboxylate

시약·촉매·용매 4

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 1140Toluene용매HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of 165 mg (0.55 mmole) 4-(1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester, 25 mg tetrabutylammonium hydrogen sulfate and 0.08 mL (0.6 mmole) benzenesulfonyl chloride in 2 mL 4 M sodium hydroxide and 5 mL toluene was stirred at room temperature for 2 hours. The mixture was diluted with 5 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 5 mL water, 5 mL saturated sodium chloride, dried (magnesium sulfate) and concentrated. 4-(1-Benzenesulfonyl-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester was isolated by recrystallization from ether/hexane, 223 mg, m.p. 143-144° C.

후처리

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 5 mL water, 5 mL saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-079b97bf846441cc836cfa9bcbc885ff
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790848B2

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