Ethylene Glycol → 4-(3-Iodophenyl)morpholine

HRID 600998

Reaktionsgleichung

Reaktionsgleichung von HRID 600998
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 545364344-(3-Iodophenyl)morpholineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fcfbfd189614470b9d6d45029dd6011
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902239B2

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