Morpholine → 4-(3,5-Dichlorophenyl)morpholine

HRID 1514948

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 3,5-dichloroiodobenzene (272 mg, 1 mmol) in anhydrous THF (3 mL) was added morpholine (200 μL, 2 mmol), catalytic (+/−) BINAP (6 mol %), catalytic Pd2(dba)3 (3 mol %) and sodium tert-butoxide (192 mg, 2 mmol). The mixture was sparged with N2 for 5 minutes, then the vial was sealed and heated at 80° C. for 18 h. The reaction mixture was directly purified via flash chromatography on silica gel, eluting with a 0-50% gradient of ethyl acetate/heptane to obtain 4-(3,5-dichlorophenyl)-morpholine as a white solid. 1H NMR (CDCl3, 400 MHz) δ 6.84 (t, J=1.71 Hz, 1H), 6.75 (d, J=1.77 Hz, 2H), 3.81-3.87 (m, 4H), 3.13-3.19 (m, 4H). MS (m/z) 232.2 (M+1).

Aufarbeitung

customThe mixture was sparged with N2 for 5 minutes
customthe vial was sealed
customThe reaction mixture was directly purified via flash chromatography on silica gel
washeluting with a 0-50% gradient of ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag: ord-06d580569c1b42948e3f24decc4c70d8
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08222248B2

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