Dimethyl Sulfoxide → 1-(3-Cyanophenyl)piperazine

HRID 551290

反応式

HRID 551290 の反応式
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CS(C)=O>O>[C:5]([C:4]1[CH:3]=[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 678803-Fluorobenzonitrile

生成物 1

HCID 114809021-(3-Cyanophenyl)piperazine収率 143.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-fluorobenzonitrile (3.0 g, 25 mmol), piperazine (11.8 g, 137 mmol) and dimethylsulphoxide (20 ml) is heated at 100° C. for 48 hours under an atmosphere of nitrogen. The reaction mixture is then cooled, poured into water (200 ml) and the resultant precipitate collected. This solid is chromatographed on silica gel (dichloromethane) to give the title compound as a white solid (6.7 g). 1H NMR (DMSO, 500 MHz) δ7.15-7.40 (m, 4H), 3.28 (m, 3H), 3.12 (m, 1H), 2.80 (m, 1H), 2.59 (m, 3H).

後処理

  1. temperatureThe reaction mixture is then cooled
  2. customthe resultant precipitate collected
  3. customThis solid is chromatographed on silica gel (dichloromethane)

出典と根拠

ORDレコード
ord-54a39dc3799e48f296756f3420669cff
出典データセット
uspto-grants-2011_05
特許番号
US07947684B2

関連ノート

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