Piperazine → 2-nitro-5-piperazin-1-yl-benzoic Acid
Reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.OS([O-])(=O)=O.[K+]>>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:13])=[O:12]Participants
Conditions
- Temperature
- 110 °C
Procedure
5-Chloro-2-nitro-benzoic acid (44 g) and piperizine (90 g, 4.8 eq.) were mixed without solvent and heated at 110° C. for 6 hours and then stirred at room temperature over night. At this time, the mixture had solidified. To this solid was added 10% KHSO4 (wt/vol, pH 4 to 5) aqueous solution and the mixture was sonicated. The supernatant was decanted and fresh 10% KHSO4 (wt/vol) aqueous solution was added. A total of 1.8 liters of 10% KHSO4 (wt/vol) aqueous solution was added and decanted in this manner. After stirring at room temperature, the solid was filtered and rinsed with water. The remaining solid was dried in a vacuum oven, leaving a yellow-orange solid (53.1 g). This material was carried forward to the next step without further purification.
Workup
- customthe mixture was sonicated
- customThe supernatant was decanted
- additionfresh 10% KHSO4 (wt/vol) aqueous solution was added
- additionA total of 1.8 liters of 10% KHSO4 (wt/vol) aqueous solution was added
- customdecanted in this manner
- stirringAfter stirring at room temperature
- filtrationthe solid was filtered
- washrinsed with water
- customThe remaining solid was dried in a vacuum oven
Sources & evidence
- ORD record
- ord-fda7825660d64536b1fa1642ec70711f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299023B2
Reaction notes
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