Water → 2-Piperazin-1-yl-benzoic acid sulfuric acid salt
Reaction equation
[C:1]([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.N1CCNCC1.[OH2:21].[OH-:22].[NH4+].[S:24](=[O:28])(=[O:27])([OH:26])[OH:25]>>[S:24](=[O:26])(=[O:25])([OH:28])[OH:27].[N:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]([OH:22])=[O:21])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1Participants
6
Conditions
- Temperature
- 100 °C
Procedure
1-(2-Cyanophenyl)piperazine (2.00 g, 10.68 mmol) was suspended in 10 mL of concentrated sulfuric acid. The piperazine slowly dissolved as the reaction mixture was heated to 100° C. After heating the reaction for 2 hr, the reaction was cooled to room temperature. 10 mL of water was added and the reaction was heated to 100° C. for another 4 hr. After cooling to room temperature, the reaction mixture was poured into 200 mL of ice water. The aqueous mixture was neutralized with ammonium hydroxide and the mixture was concentrated under vacuum. The product was extracted from the inorganic salts by washing with 25% methanol in tetrahydrofuran. The crude material was used in the next step without purification.
Workup
- temperatureAfter heating
- customthe reaction for 2 hr
- temperaturethe reaction was cooled to room temperature
- temperaturethe reaction was heated to 100° C. for another 4 hr
- temperatureAfter cooling to room temperature
- concentrationthe mixture was concentrated under vacuum
- extractionThe product was extracted from the inorganic salts
- washby washing with 25% methanol in tetrahydrofuran
- customThe crude material was used in the next step without purification
Sources & evidence
- ORD record
- ord-a0c7bb0dc7814a95ab0140e37799f5cd
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013156B2
Reaction notes
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