Nitrogen → HCID 59442053, compound
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+].[CH:63]([N:66]1[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]1)([CH3:65])[CH3:64]>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>[CH3:64][CH:63]([N:66]1[CH2:71][CH2:70][N:69]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=2)[CH2:68][CH2:67]1)[CH3:65]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To an N2 degassed solution of 1,4-dioxane (50 mL, Aldrich) was added 4-bromo-1-(methyloxy)-2-nitrobenzene (1.0 g, 4.31 mmol, Aldrich), XANTPHOS (0.74 g, 1.28 mmol, Aldrich), Pd2(dba)3(0.79 g, 0.86 mmol, Aldrich), Cs2CO3 (2.8 g, 8.63 mmol, Aldrich), and 1-isopropylpiperazine (1.10 g, 8.6 mmol, Oakwood Chemicals). After heating overnight at 90° C., the reaction was diluted with ethyl acetate (50 mL), washed with water (50 mL), organic layer adsorbed to silica gel and purified by column chromatography (dichloromethane to 5% methanol/dichloromethane) to afford 1-(1-methylethyl)-4-[4-(methyloxy)-3-nitrophenyl]piperazine (0.66 g, 55%). ESIMS (M+H)+=280.
Workup
- washwashed with water (50 mL), organic layer
- custompurified by column chromatography (dichloromethane to 5% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-21e40ee8c5a14311bf6ef78d612718b1
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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