Water → HCID 59441982, compound

HRID 1014263Notes

Reaction equation

HRID 1014263 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])[CH3:21].O>CS(C)=O>[CH3:21][CH:20]([N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[CH3:13])[CH2:25][CH2:24]1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Product 1

HCID 59441982HCID 59441982, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (1.3 g, 7.03 mmol) in dimethylsulfoxide was added potassium carbonate (1.9 g, 14.0 mmol) and isopropylpiperazine (2.0 mL, 14 mmol). The resulting suspension was warmed at 70° C. for 12 hours, poured into water, and extracted with diethyl ether. The ether layers were washed with aqueous saturated sodium chloride, dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 to afford 1-(1-methylethyl)-4-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperazine (1.78 g, 86% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm. 1.11 (d, J=6.60 Hz, 6 H), 2.24 (s, 3 H), 2.72 (s, 4 H), 2.79 (s, 1 H), 3.06 (s, 4 H), 3.93 (s, 3 H), 6.57 (s, 1 H), 7.81 (s, 1 H).

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether layers were washed with aqueous saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. custompurified by chromatography on SiO2

Sources & evidence

ORD record
ord-c63c6f1da2c94e968aa80bfef6fbb3aa
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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