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

HRID 734821노트

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HRID 734821 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e5100dc3466a4523bf2d8274b0469681
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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