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

HRID 132912

반응식

HRID 132912 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-684344737d874f748b52592cd98fb8a5
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388011B2

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