Morpholine → 4-(4-Methoxy-3-nitrophenyl)morpholine

HRID 1804704Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>O1CCOCC1.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]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 20 ml vial was charged 4-bromo-1-methoxy-2-nitrobenzene (0.3 g, 1.293 mmol), morpholine (0.338 ml, 3.88 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.059 g, 0.065 mmol), xantphos (0.037 g, 0.065 mmol) and sodium tert-butoxide (0.311 g, 3.23 mmol) in 1,4-dioxane (12.93 ml). The reaction mixture was heated at 100° C. on a hot plate for 2 hours. The solution was allowed to cool and stir overnight at room temperature. The mixture was concentrated and the residue was loaded onto a silica gel column. The compound was eluted using a gradient starting with 100% dichloromethane to 1:1 dichloromethane/methanol over 50 minutes to provide the title compound. MS (DCI(+)) m/e 239.0 (M+H)+.

Workup

temperatureto cool
concentrationThe mixture was concentrated
washThe compound was eluted
waitstarting with 100% dichloromethane to 1:1 dichloromethane/methanol over 50 minutes

Sources & evidence

ORD record: ord-3ce735e8c5aa40ab8a382a58a2216688
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354422B2

Reaction notes

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