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

HRID 1708378Notes

Reaction equation

HRID 1708378 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

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

Product 1

HCID 37831381-(2-methoxy-5-nitrophenyl)piperazineYield 76.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (6.06 g) was added portionwise during 2 h to a solution of 1-(2-methoxyphenyl)piperazine ( 10.0 g) in sulphuric acid (50 ml; 95%) at room temperature. The resulting brown solution was stirred at room temperature for 30 min and added cautiously to ice (300 ml). The solution was basified with aqueous sodium hydroxide (5N) and extracted with ethyl acetate (2×400 ml). The dried extract was evaporated and the residue was purified on a column of silica (190:10:1) to give the title compound as a yellow solid (9.4 g). m.p. 102°-104° C.

Workup

  1. extractionextracted with ethyl acetate (2×400 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified on a column of silica (190:10:1)

Sources & evidence

ORD record
ord-8773250e295742a6b3e08e7a700fe625
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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