Water → Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

HRID 131204

반응식

HRID 131204 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>CS(C)=O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

참가 물질

5

반응물 3

HCID 962WaterHCID 742185-Chloro-2-nitroanilineHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 22272542Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 2 g (11.6 mmol) 5-chloro-2-nitro-phenylamine, 2.14 g (11.6 mmol) piperazine-1-carboxylic acid tert-butyl ester and 1.3 g (11.6 mmol) 1,4-diazo-bicyclo[2.2.2]octane in 20 ml DMSO was heated to 150° C. for 16 h. The mixture was poured onto 200 ml water and extracted with 250 ml ethyl acetate. The emulsion was filtered through decalite and the aqueous phase was extracted with 2×200 ml. The combined organic phases were washed with 2×100 ml water, dried with MgSO4 and evaporated to dryness. The residue was purified with column chromatography on silica eluting with ethyl acetate/hexane to yield the title compound as a yellow solid. MS(ISP): 321.2 (M−H)−.

후처리

  1. extractionextracted with 250 ml ethyl acetate
  2. filtrationThe emulsion was filtered through decalite
  3. extractionthe aqueous phase was extracted with 2×200 ml
  4. washThe combined organic phases were washed with 2×100 ml water
  5. dry with materialdried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified with column chromatography on silica eluting with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-e9dd066e945449a0a2be19e1e5a159d2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384945B2

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