Sodium Carbonate → 1-(3,4-Difluorophenyl)piperazine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C(=O)([O-])[O-].[Na+].[Na+].Cl.Cl[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]Cl>C(O)CCC>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:6]=[CH:7][C:8]=1[F:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
3,4-Difluoro-aniline (1 g, 7.7 mmol) was dissolved in dry n-butanol (10 mL) and dry sodium carbonate (3.2 g, 30 mmol) was added to it and the reaction mixture stirred for 1 hour under nitrogen. Bis(2-chloroethyl) amine hydrochloride (1.38 g, 7.7 mmol) in nBuOH (10 mL) were then added to the mixture via a syringe. The reaction was then heated at 120° C. for 48 h. The nBuOH was evaporated in vacuo and the residue was extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration afforded the crude product. Purification using flash column chromatography (chloroform/methanol) afforded 1-(3,4-Difluoro-phenyl)-piperazine as an off white solid.
Workup
- customThe nBuOH was evaporated in vacuo
- extractionthe residue was extracted with ethyl acetate
- dry with materialDrying of the organic layer with Na2SO4
- concentrationfollowed by concentration
- customafforded the crude product
- customPurification
Sources & evidence
- ORD record
- ord-1bbdea8a8d4044fb8ecb7550684f443b
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449576B1
Reaction notes
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