1,10-Phenanthroline → 3-(4-Bromo-phenoxy)-1-ethyl-piperidine

HRID 1916573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916573
C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.[CH2:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH:33]([OH:37])[CH2:32]1)[CH3:30]>C1(C)C=CC=CC=1.[Cu]I.CCOC(C)=O.O>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([O:37][CH:33]2[CH2:34][CH2:35][CH2:36][N:31]([CH2:29][CH3:30])[CH2:32]2)=[CH:24][CH:23]=1

Komponenten

9

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 1145241-Ethyl-3-piperidinol

Produkt 1

HCID 673628503-(4-Bromo-phenoxy)-1-ethyl-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

652 mg (2.00 mmol) caesium carbonate, 36 mg (0.20 mmol) 1,10-phenanthroline and 19 mg (0.10 mmol) CuI are added to a solution of 289 mg (1.00 mmol) 1-bromo-4-iodobenzene and 0.27 mL (2.00 mmol) N-ethyl-3-hydroxypiperidine in 1.0 mL toluene. The reaction mixture is stirred for 36 h at 110° C. and then combined with 10 mL water and 10 mL EtOAc. After filtration the aqueous phase is extracted with 10 mL EtOAc and the combined organic extracts are washed with saturated NaCl solution and dried over Na2SO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (EtOAc).

Aufarbeitung

  1. filtrationAfter filtration the aqueous phase
  2. extractionis extracted with 10 mL EtOAc
  3. washthe combined organic extracts are washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customand further purification

Quellen und Nachweise

ORD-Eintrag
ord-1db55905c8f44b77ac647a879838b357
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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