Water → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine

HRID 419657노트

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HRID 419657 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([CH3:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[CH3:14][O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][O:15][CH3:14])[CH2:19][CH2:20]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27346381-(2-Methoxyethyl)piperazineHCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

생성물 1

HCID 594526231-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methyloxy)ethyl]piperazine수율 86.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
130 °C

실험 절차

To 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (prepared according to Example 113, Step B) (1 g, 5.4 mmol) in 10 mL of DMSO was added, 1-[2-(methyloxy)ethyl]piperazine (1 g, 7 mmol), and K2CO3 (1.27 g, 4.2 mmol). The mixture was heated to 130° C. for 24 h. The mixture was then poured into 100 mL of H2O and extracted with EtOAc. The product was isolated by flash chromatography to give the title compound of step A (1.44 g, 4.65 mmol, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.74 (s, 1H), 6.68 (s, 1H), 3.88 (s, 3H), 3.44 (t, J=5.68 Hz, 2H), 3.22 (s, 3H), 2.95-3.01 (m, 4H), 2.50-2.58 (m, 6H), 2.17 (s, 3H).

후처리

  1. extractionextracted with EtOAc
  2. customThe product was isolated by flash chromatography

출처 및 근거

ORD 기록
ord-3e9e969f373e41a48df7ebb2ef45c5b1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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