Potassium Carbonate → 1-Boc-4-(2-chloro-6-nitrophenyl)piperazine

HRID 132912

反応式

HRID 132912 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1Cl.[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].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:3]2[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 185552,3-DichloronitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 587677041-Boc-4-(2-chloro-6-nitrophenyl)piperazine収率 70.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 1,2-dichloro-3-nitrobenzene (0.96 g, 5.0 mmol) and piperazine-1-carboxylic acid tert-butyl ester (0.93 g, 5.0 mmol) in acetonitrile (5 mL) was added of K2CO3 (1.38 g, 10 mmol). The mixture was heated at reflux for 48 h. The solvent was removed under reduced pressure. The crude material was partitoned between EtOAc (100 mL) and H2O (20 mL). The organic layer was washed with H2O (2×20 mL), dried over Na2SO4 and concentrated. Column chromatography (silica, 10-20% EtOAc/hexanes) provided 4-(2-chloro-6-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.2 g, 70%). TLC (silica, 20% EtOAc/hexanes): Rf=0.45. MS (electrospray): exact mass calculated for C15H20CIN3O4, 341.1; m/z found, 364.1 [M+Na]30 . 1H NMR (400 MHz, CDCl3) 7.56 (dd, J=8.2, 1.4 Hz, 1H), 7.50 (dd, J=8.2, 1.4 Hz, 1H), 7.13 (t, J=8.2 Hz, 1H), 3.38-3.56 (m, 4H), 3.06 (m, 4H), 1.48 (s, 9H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed under reduced pressure
  4. washThe organic layer was washed with H2O (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-684344737d874f748b52592cd98fb8a5
出典データセット
uspto-grants-2008_06
特許番号
US07388011B2

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