Triethylamine → 4-(4-Fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C1COCC1>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][C:22]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)=[O:23])=[CH:30][CH:29]=1)([O-:33])=[O:32]Participants
Conditions
- Temperature
- 0 °C
Procedure
1-(4-Fluoro-phenyl)-piperazine (12.2 g, 67.7 mmol) and triethylamine (4.63 mL, 67.7 mmol) were dissolved in anhydrous THF (150 mL) under nitrogen and the reaction mixture was cooled to 0° C. 4-Nitrophenyl chloroformate (13.4 g, 67.7 mmol) dissolved in anhydrous THF (150 mL) at 0° C. was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue suspended between water and EtOAc. The aqueous layer was extracted with two further portions of EtOAc, the organic layers were combined, dried (MgSO4), dried in vacuo and then recrystallised from toluene (50 mL)/hexane (60 mL) to give 4-(4-fluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester (15.8 g, 67%) as fine yellow needles.
Workup
- additionwas added
- customThe solvent was removed in vacuo
- extractionThe aqueous layer was extracted with two further portions of EtOAc
- dry with materialdried (MgSO4)
- customdried in vacuo
- customrecrystallised from toluene (50 mL)/hexane (60 mL)
Sources & evidence
- ORD record
- ord-97e67a0b8d264d1c9a18424c2126d1a0
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851471B2
Reaction notes
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