Sulfuric Acid → 1-(2-methoxy-5-nitrophenyl)piperazine
Reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[N+:20]([O-])([O-:22])=[O:21].[K+].C(=O)([O-])[O-].[Na+].[Na+]>>[N:1]1([C:7]2[CH:12]=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1Participants
Procedure
2-(Piperazin-1-yl)anisole (5.1 g; 26 mmol) is acidified slowly with 6 ml of sulfuric acid (5N) and then dehydrated by evaporation under reduced pressure. Concentrated sulfuric acid is then added (22 ml) very slowly (25 min) and the reaction medium is stirred until a homogeneous mixture is obtained. Potassium nitrate (3.1 g; 31 mmol) is added portionwise over 35 minutes. The reaction is stirred for 4 hours. The solution is then poured onto ice and neutralized by addition of sodium carbonate (to pH≈7-8). The nitro derivative is extracted from the aqueous phase with ethyl acetate (4×80 ml), dried over magnesium sulfate and purified by flash chromatography with an eluent gradient (2 to 5% methanol in dichloromethane in the presence of 0.5% aqueous ammonia).
Workup
- customdehydrated by evaporation under reduced pressure
- additionConcentrated sulfuric acid is then added (22 ml) very slowly (25 min)
- customis obtained
- stirringThe reaction is stirred for 4 hours
- additionThe solution is then poured onto ice
- extractionThe nitro derivative is extracted from the aqueous phase with ethyl acetate (4×80 ml)
- dry with materialdried over magnesium sulfate
- custompurified by flash chromatography with an eluent gradient (2 to 5% methanol in dichloromethane in the presence of 0.5% aqueous ammonia)
Sources & evidence
- ORD record
- ord-80f9db0221274a2fa42a763bcac91eac
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789412
Reaction notes
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