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

HRID 49031

반응식

HRID 49031 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 206351751-(2-Hydroxyethyl)-4-(2-fluorophenyl)piperazine수율 65.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-74e89468e2c345a2a19678b9a39c2698
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706716B2

연결된 노트

불러오는 중…