Potassium Carbonate → 1-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine

HRID 518813Notes

Reaction equation

HRID 518813 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:15][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][CH:12]([CH3:14])[CH3:13])[CH:3]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzene

Product 1

HCID 866979831-Methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazineYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 10.0 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene, 10.0 g of 1-methylpiperazine and 10.4 g of potassium carbonate in 93 ml of DMSO is stirred at ambient temperature overnight. The mixture is diluted with 160 ml of water and extracted three times with 150 ml of ethyl acetate. The organic phases are dried over magnesium sulfate and concentrated under vacuum. The residue is purified on 200 g of silica, elution being carried out with dichloromethane/methanol (98/2 then 95/5), so as to obtain 13.6 g of 1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine in the form of a yellow oil.

Workup

  1. extractionextracted three times with 150 ml of ethyl acetate
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue is purified on 200 g of silica, elution

Sources & evidence

ORD record
ord-1b1f6372aca04743aa148a4577efee38
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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