Potassium Carbonate → 1-(2-Hydroxyethyl)-4-(2-fluorophenyl)piperazine

HRID 49031

反応式

HRID 49031 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.I[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:17][CH2:16][CH2:15][N:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][CH2:10]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 705291-(2-Fluorophenyl)piperazine

生成物 1

HCID 206351751-(2-Hydroxyethyl)-4-(2-fluorophenyl)piperazine収率 65.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 1-(2-fluorophenyl)piperazine (0.50 g), 2-iodoethanol (0.48 g), and potassium carbonate (1.5 g) in dimethylformamide (7 mL) was heated at reflux for three hours. The solvent was removed in vacuo and the residue was purified by preparative thin-layer chomatography (silica gel, eluting with chloroform/methanol, 9:1), giving the title compound as a yellow oil (0.41 g, 65%). 1H NMR (300 MHz, CDCl3) δ7.09-6.90 (m, 4H), 3.67 (t, 2H, J=5.4 Hz), 3.13 (t, 4H, J=4.7 Hz), 2.76 (br s, 1H), 2.71 (t, 4H, J=4.8 Hz), 2.63 (t, 4H, J=5.4 Hz). 13C NMR (75 MHz, CDCl3) δ156.3 (d, J=244.1 Hz), 140.6 (d, J=8.8 Hz), 125.1 (d, J=3.4 Hz), 123.2 (d, J=8.1 Hz), 119.5 (d, J=2.9 Hz), 116.7 (d, J=20.6 Hz), 60.1, 58.4, 53.6 (2C), 51.2 (d, 2C, J=3.0 Hz).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by preparative thin-layer chomatography (silica gel, eluting with chloroform/methanol, 9:1)

出典と根拠

ORDレコード
ord-74e89468e2c345a2a19678b9a39c2698
出典データセット
uspto-grants-2004_03
特許番号
US06706716B2

関連ノート

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