Ethylene Glycol → 4-(3-Iodophenyl)morpholine

HRID 600998

반응식

HRID 600998 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[I:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 8083MorpholineHCID 12270Benzene, 1,3-diiodo-HCID 62657Potassium Phosphate, Tribasic

생성물 1

HCID 545364344-(3-Iodophenyl)morpholine수율 41%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1,3-diiodobenzene (5.05 g, 15.3 mmol) in isopropanol (16 mL) under nitrogen was added morpholine (1.33 g, 1.33 mL, 15.3 mmol), potassium phosphate (6.50 g, 30.6 mmol), ethylene glycol (1.90 g, 1.70 mL, 30.6 mmol) and copper (I) iodide (146 mg, 0.765 mmol). The mixture was heated at 80° C. for 15 h, and then cooled to room temperature. The solids were removed by filtration and the solution was concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (5 to 25% EtOAc) to give 4-(3-iodo-phenyl)-morpholine (1.81 g, 41%) as a colorless oil. MS (ES+): m/z=290.0; 1H NMR (CDCl3, 500 MHz): δ 3.15 (t, 4H), 3.85 (t, 4H), 6.87 (dd, 1H), 6.96-7.00 (m, 1H), 7.20 (d, 1H), 7.22-7.25 (m, 1H).

후처리

  1. temperaturecooled to room temperature
  2. customThe solids were removed by filtration
  3. concentrationthe solution was concentrated
  4. customThe residue was purified by silica gel column chromatograghy
  5. washeluted with EtOAc

출처 및 근거

ORD 기록
ord-4fcfbfd189614470b9d6d45029dd6011
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902239B2

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