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

HRID 1358930Notes

Reaction equation

HRID 1358930 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+].[OH-].[Na+]>S(=O)(=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

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 14798Sodium HydroxideHCID 24434Potassium Nitrate

Product 1

HCID 37831381-(2-methoxy-5-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 5M sulphuric acid (114 ml) was added over 0.3 h to 1-(2-methoxyphenyl)piperazine (110 g) at 0° C. with stirring. To the ice-cooled stirred slurry was then added, over 1.75 h, concentrated sulphuric acid (560 ml) and the temperature was maintained for a further 1.5 h. Potassium nitrate (71.5 g) was then added portionwise over 1.5 h to the stirred, cold, viscous mixture which was then left to stand for 18 h. The solution was poured onto ice (2 Kg) and the resulting cooled mixture brought to pH 12 by the addition of 40% sodium hydroxide solution. The oily mixture was extracted with ethyl acetate (2×2L) and the combined organic extracts were washed with water (3L), dried (Na2SO4), concentrated to a residue which was stirred with diethyl ether (700 ml) to give the title compound (D1) as a yellow solid, m.p. 84-87° C. (95 g, 70%). MH+238.

Workup

  1. stirringstirred slurry
  2. additionwas then added, over 1.75 h
  3. waitcold, viscous mixture which was then left
  4. additionThe solution was poured onto ice (2 Kg)
  5. temperaturethe resulting cooled mixture
  6. extractionThe oily mixture was extracted with ethyl acetate (2×2L)
  7. washthe combined organic extracts were washed with water (3L)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to a residue which
  10. stirringwas stirred with diethyl ether (700 ml)

Sources & evidence

ORD record
ord-f8539b946faf46ab9a520a0a1e3f7535
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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