1,10-Phenanthroline → N-(3-morpholin-4-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 600999

Reaktionsgleichung

I[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:14]([O:18][C:19](=[O:22])[NH:20][NH2:21])([CH3:17])([CH3:16])[CH3:15].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu]I.O>[C:14]([O:18][C:19]([N:20]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:3]=1)[NH2:21])=[O:22])([CH3:17])([CH3:16])[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 4-(3-iodo-phenyl)-morpholine (1.81 g, 6.26 mmol) in DMF (6.5 mL) under nitrogen was added tert-butylcarbazate (993 mg, 7.52 mmol), copper (I) iodide (59.5 mg, 0.313 mmol), 1,10-phenanthroline (113 mg, 0.626 mmol) and cesium carbonate (2.85 g, 8.77 mmol). The mixture was heated at 80° C. for 18 h and then cooled to room temperature. Water (100 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (25 to 50% EtOAc) to give N-(3-morpholin-4-yl-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.14 g, 62%) as a yellowi oil. MS (ES+): m/z=294.2. 1H NMR (DMSO-d6, 500 MHz): δ 1.44 (s, 9H), 3.06 (t, 4H), 3.73 (t, 4H), 4.97 (s, 2H), 6.66 (dd, 1H), 6.91 (d, 1H), 7.01-7.05 (m, 1H), 7.09-7.14 (m, 1H).

Aufarbeitung

temperaturecooled to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatograghy
washeluted with EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-5fbda8b809dd43cf9868a0ec889ba50f
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07902239B2

Verknüpfte Notizen

Wird geladen…