Water → N-[1-(2-Amino-benzoyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

HRID 1428961노트

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HRID 1428961 반응식
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:34])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-])=O)[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[NH4+].[Cl-].O>C1(C)C=CC=CC=1.CCOC(C)=O.[Fe]>[NH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]([N:21]1[CH2:22][CH2:23][CH:18]([N:4]([CH:1]2[CH2:3][CH2:2]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:19][CH2:20]1)=[O:34]

참가 물질

7

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 24860818N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide

생성물 1

HCID 24860819N-[1-(2-Amino-benzoyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide수율 88.5%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
115 °C

실험 절차

N-Cyclopropyl-N-[1-(2-nitro-benzoyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide (10) (0.403 mg, 0.81 mmol) was taken up in 7 ml of toluene. To the mixture, Fe (0.230 mg, 4.1 mmol), NH4Cl (0.440 g, 8.2 mmol) and H2O (0.8 ml) was added. The reaction mixture was heated at 115° C. and stirred for 3 hours. The reaction mixture was diluted with 30 ml of EtOAc, then filtrated by Celite. The filtration was concentrated and dryness under reduced pressure. The crude product was purified through a column of silica gel with a gradient of 35% to 80% EtOAc in hexane to afford the title compound 11 (pale yellow solid, 335 mg, 88%). LC: 100%. MS: m/z=467.

후처리

  1. filtrationfiltrated by Celite
  2. filtrationThe filtration
  3. concentrationwas concentrated
  4. customThe crude product was purified through a column of silica gel with a gradient of 35% to 80% EtOAc in hexane

출처 및 근거

ORD 기록
ord-4709f06ee9294186a261b15b7dc64a49
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937181B2

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