1-(2-Methoxyphenyl)piperazine → 1-(2-methoxy-5-nitrophenyl)piperazine

HRID 1157602Notes

Reaction equation

HRID 1157602 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[N+:15]([O-])([O-:17])=[O:16].[K+]>OS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:15]([O-:17])=[O:16])=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 24434Potassium Nitrate

Product 1

HCID 37831381-(2-methoxy-5-nitrophenyl)piperazineYield 42%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 1-[2-(methyloxy)phenyl]piperazine (11.0 g, 50.7 mmol) was added concentrated H2SO4 (60 mL) dropwise to and stirred for 4 h at 0° C. KNO3 (7.2 g, 71.2 mmol) was then added and the mixture stirred overnight while allowing to warm to rt. Reaction was then quenched with ice and then 2N NaOH (100 mL) added and extracted three times with EtOAc. Combined organic phases were dried over MgSO4 and loaded directly onto silica gel. Purified by silica gel chromatography in 0-20% MeOH/NH4OH in EtOAc. Yield 5.7 g, 42% yield, of an orange solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.8 (m, 4H) 2.9 (m, 4H) 3.1 (m, 1H) 3.9 (s, 3H) 7.1 (d, J=9.1 Hz, 1H) 7.6 (d, J=2.7 Hz, 1H) 7.9 (dd, J=9.0, 2.7 Hz, 1H).

Workup

  1. stirringthe mixture stirred overnight
  2. temperatureto warm to rt
  3. customReaction
  4. customwas then quenched with ice
  5. addition2N NaOH (100 mL) added
  6. extractionextracted three times with EtOAc
  7. dry with materialCombined organic phases were dried over MgSO4
  8. customPurified by silica gel chromatography in 0-20% MeOH/NH4OH in EtOAc

Sources & evidence

ORD record
ord-d7696b7992954d799fa77e2c0d90858e
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…