Potassium Carbonate → 1-[2-Methyl-5-(ethyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 419666

反応式

HRID 419666 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH2:12][CH3:13])=[CH:4][C:3]=1F.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:22][S:23]([CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:25])=[O:24]>CS(C)=O.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH2:12][CH3:13])=[CH:4][C:3]=1[N:31]1[CH2:30][CH2:29][N:28]([CH2:27][CH2:26][S:23]([CH3:22])(=[O:24])=[O:25])[CH2:33][CH2:32]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 594528831-Ethoxy-5-fluoro-4-methyl-2-nitrobenzeneHCID 666496671-[2-(Methylsulfonyl)ethyl]piperazine hydrochloride

生成物 1

HCID 594527341-[2-Methyl-5-(ethyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine収率 90.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

1-Methyl-2-fluoro-4-(ethyloxy)-5-nitrobenzene (Example 215, step A) (5.74 g, 28.8 mmol) was dissolved in DMSO (60 mL). K2CO3 (11.9 g, 86.4 mmol) and 1-[2-(methylsulfonyl)ethyl]piperazine hydrochloride (Example 148, step B) (9.85 g, 43.2 mmol) were added and the reaction mixture was heated to 100° C. and allowed to stir overnight. The mixture was cooled to rt then diluted with DCM and filtered. The filtrate was poured into H2O and extracted with DCM. The combined organics were dried with MgSO4, filtered, and concentrated in vacuo to give the title compound of Step A (9.70 g, 26.1 mmol, 90%) as an orange solid. 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H), 6.51 (s, 1H), 4.11 (q, J=7.0 Hz, 2H), 3.16 (t, J=6.5 Hz, 2H), 3.03 (s, 3H), 3.00-2.91 (m, 6H), 2.72-2.62 (m, 4H), 2.21 (s, 3H), 1.44 (t, J=7.0 Hz, 3H).

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered
  3. additionThe filtrate was poured into H2O
  4. extractionextracted with DCM
  5. dry with materialThe combined organics were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5c424a4468b349a1b55325fe61d26e26
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

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