Cesium carbonate → 1-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][CH:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:15].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+]>O1CCOCC1.CCOC(C)=O.O.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]>[CH3:13][CH:14]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=2)[CH2:18][CH2:17]1)[CH3:15]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
To 4-chloro-2-(methyloxy)-1-nitrobenzene (3.0 g, 16.0 mmol) in dioxane (75 mL) was added 1-(1-methylethyl)piperazine (4.1 g, 32.0 mmol), XANTPHOS (1.4 g, 2.4 mmol), and Cs2CO3 (10.4 g, 32.0 mmol). The mixture was bubbled with N2 for 15 min prior to the addition of Pd2(dba)3 (1.5 g, 1.6 mmol). The reaction was stirred at 100° C. for 5 h. Following cooling to rt, the reaction mixture was diluted with EtOAc (150 mL) and H2O (100 mL). The organic layer was dried over NaSO4 taken to a residue under reduced pressure, and purified by silica gel chromatography to afford the title compound of step A (4.0 g, 90% yield). MS (ESI) (M+H)+=280.
Workup
- customThe mixture was bubbled with N2 for 15 min
- temperatureFollowing cooling to rt
- dry with materialThe organic layer was dried over NaSO4
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-f2e98b83387343128741cb9ca1ef9ed5
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093239B2
Reaction notes
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