1-Bromo-4-nitrobenzene → 1-Ethyl-4-(4-nitrophenyl)piperazine

HRID 409665

반응식

HRID 409665 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12]>O.C(Cl)Cl.CO>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1)[CH3:12]

참가 물질

5

반응물 2

HCID 114661-Bromo-4-nitrobenzeneHCID 791961-Ethylpiperazine

생성물 1

HCID 28575491-Ethyl-4-(4-nitrophenyl)piperazine

시약·촉매·용매 2

HCID 962Water용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1-bromo-4-nitrobenzene (6 g, 29.7 mmol) and 1-ethylpiperazine (7.6 mL, 59.4 mmol, 2 equiv) is heated to 80° C. for 15 h. After cooling to RT, the reaction mixture is diluted with water and DCM/MeOH, 9:1. The aqueous layer is separated and extracted with DCM/MeOH, 9:1. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) affords the title compound as a yellow solid: ESI-MS: 236.0 [MH]+; tR=2.35 min (purity: 100%, system 1); TLC: Rf=0.50 (DCM/MeOH+1% NH3aq, 9:1).

후처리

  1. temperatureAfter cooling to RT
  2. customThe aqueous layer is separated
  3. extractionextracted with DCM/MeOH, 9:1
  4. washThe organic phase is washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

출처 및 근거

ORD 기록
ord-f404d9e1f79343e5b53672e82eea05b4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759517B2

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