Toluene → 1-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine

HRID 502701Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CC(C)([O-])C.[Na+].C1(C)C=CC=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].C(OCC)(=O)C.O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 50 mL round bottom flask was placed the 1-iodo-3-nitro-5-(trifluoromethyl)benzene (1 g, 3.15 mmol), N-methylpiperazine (0.379 g, 3.78 mmol), bis(dibenzylideneacetone)palladium (0.029 g, 0.0315 mmol), sodium tert-butoxide (0.424 g, 4.416 mmol), 2-dicyclohexyl-2′-(N,N-dimethylamino)biphenyl (0.037 g, 0.094 mmol), and toluene (25 mL). Reaction was heated to 80° C. with stirring for 20 hours. Reaction was cooled to room temperature and water (1 mL) and ethyl acetate (10 mL) were added. The organic layer is separated, concentrated under reduced pressure and purified via silica column eluting with 0 to 20% methanol in dichloromethane. The title compound was obtained as an orange oil.

Workup

customInto a 50 mL round bottom flask was placed
customReaction
customReaction
temperaturewas cooled to room temperature
customThe organic layer is separated
concentrationconcentrated under reduced pressure
custompurified via silica column
washeluting with 0 to 20% methanol in dichloromethane

Sources & evidence

ORD record: ord-b2eb7fa5ef4f49e2acb762ffdd6afeee
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776869B2

Reaction notes

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