Nitrogen → 1-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine

HRID 1014217Notes

Reaction equation

N#N.Br[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=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.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:63][N:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1>C(OCC)(=O)C.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].O1CCOCC1>[CH3:63][N:64]1[CH2:69][CH2:68][N:67]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=2)[CH2:66][CH2:65]1

Participants

Conditions

Temperature: 90 °C

Procedure

To an N2 degassed solution of 1,4-dioxane (20 mL), was added 4-bromo-1-(methyloxy)-2-nitrobenzene (0.5 g, 2.16 mmol), XANTPHOS (0.37 g, 0.65 mmol, Aldrich), Pd2(dba)3(0.39 g, 0.43 mmol, Aldrich), Cs2CO3 (1.4 g, 4.3 mmol, Aldrich), and 1-methylpiperazine (0.43 g, 4.3 mmol, Aldrich). After heating overnight at 90° C., the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL), the organic layer adsorbed to silica gel and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to afford 1-methyl-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.4 g, 74%) as a tan solid. ESIMS (M+H)+=252.

Workup

washwashed with water (50 mL)
custompurified by column chromatography (dichloromethane to 5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-ae041231a94b47ae9f511ff9e250adc5
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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