Acetic Acid → 1-Nitroso-4-(2,2,2-trifluoroethyl)piperazine
Reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[N:12]([O-])=[O:13].[Na+].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[N:12]([N:7]1[CH2:6][CH2:5][N:4]([CH2:3][C:2]([F:1])([F:10])[F:11])[CH2:9][CH2:8]1)=[O:13]Participants
7
Procedure
To a solution of 1-(2,2,2-trifluoroethyl)piperazine (4.88 g, 29.0 mmol) in water (4.9 mL) that cooled with ice bath, a solution of sodium nitrite (4.04 g, 58.6 mmol) in water (20 mL) and acetic acid (5.0 mL, 87.0 mmol) were added dropwise slowly, then the mixture was stirred for 1 h. The reaction mixture was all owed to warm to ambient temperature, stirred for further 2 h. The reaction mixture was adjusted to pH9 using sodium carbonate, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated to afford 1-nitroso-4-(2,2,2-trifluoroethyl)piperazine as oil (5.57 g, y. 97%).
Workup
- stirringstirred for further 2 h
- washwashed with water and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4da62a82c56d468a8489f3d58f90a5de
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742113B2
Reaction notes
Loading…