Potassium Carbonate → HCID 59442097, compound

HRID 1014258Notes

Reaction equation

HRID 1014258 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N:19]2[CH2:20][CH2:21][N:16]([CH:13]([CH3:15])[CH3:14])[CH2:17][CH2:18]2)[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 780131-IsopropylpiperazineHCID 132515092-Chloro-4-fluoro-3-methyl-1-nitrobenzene

Product 1

HCID 59442097HCID 59442097, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

To the solution of 2-chloro-4-fluoro-3-methyl-1-nitrobenzene (12.5 g, 64.8 mmol, 1.2 equiv.) and isopropylpiperazine (10.8 g, 53.98 mmol, 1 equiv.) in 90 mL of anhydrous DMSO was added powdered K2CO3 (37 g, 269 mmol, 5 equiv.). The mixture was stirred at 40-50° C. overnight before it was poured into 200 mL of ice-water. The precipitates were collected and purified via chromatography on SiO2 to afford 1-(3-chloro-2-methyl-4-nitrophenyl)-4-(1-methylethyl)piperazine as a yellow solid (12.7 g, 79% Yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.95-1.05 (d, J=6.53 Hz, 6H), 2.31 (s, 3H), 2.60-2.72 (m, 5H), 2.89-2.95 (m, 4H), 6.87 (d, J=8 Hz, 1H), 7.62 (d, J=8 Hz, 1H).

Workup

  1. customThe precipitates were collected
  2. custompurified via chromatography on SiO2

Sources & evidence

ORD record
ord-bfeb9d005f3c48c99d1fc49378506e27
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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