4-Iodophenol → 1-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidine

HRID 734821ノート

反応式

HRID 734821 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 30170521-(2-Chloroethyl)-4-methylpiperidine

生成物 1

HCID 690610171-(2-(4-Iodophenoxy)ethyl)-4-methylpiperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A suspension of 1.55 g (52.50 mmol) of 4-iodophenol, 8.50 g (52.57 mmol) of 1-(2-chloroethyl)-4-methylpiperidine, and 14.51 g (105.00 mmol) of potassium carbonate in 200 mL of DMF was stirred for 6 hours at 80° C., the reaction mixture was cooled to RT, filtered, and the filtrate was evaporated down in vacuo. The residue was taken up in EtOAc, and the organic phase was washed with 2M aqueous NaOH solution, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, gradient EtOAc/MeOH/sat. aqueous ammonia 100:0:0→95:5:0.5). Yield: 12.90 g (71% of theoretical); C14H20INO (M=345.219); calc.: molpeak (M+H)+: 346; found: molpeak (M+H)+: 346; Rf value: 0.30 (silica gel, DCM/MeOH/sat. aqueous ammonia 95:5:0.5).

後処理

  1. temperaturethe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. customthe filtrate was evaporated down in vacuo
  4. washthe organic phase was washed with 2M aqueous NaOH solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated down in vacuo
  7. customThe crude product was purified by column chromatography (silica gel, gradient EtOAc/MeOH/sat. aqueous ammonia 100:0:0→95:5:0.5)

出典と根拠

ORDレコード
ord-e5100dc3466a4523bf2d8274b0469681
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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