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

HRID 419657ノート

反応式

HRID 419657 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3e9e969f373e41a48df7ebb2ef45c5b1
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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