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

HRID 131204

反応式

HRID 131204 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-e9dd066e945449a0a2be19e1e5a159d2
出典データセット
uspto-grants-2008_06
特許番号
US07384945B2

関連ノート

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