Potassium Carbonate → rel-(3R,5S)-1-[4-Chloro-5-(trifluoromethyl)-2-pyridinyl]-3,5-dimethylpiperazine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH3:13][CH:14]1[CH2:19][NH:18][CH2:17][CH:16]([CH3:20])[NH:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([N:18]2[CH2:17][C@H:16]([CH3:20])[NH:15][C@H:14]([CH3:13])[CH2:19]2)[CH:7]=1Participants
5
Conditions
- Temperature
- 140 °C
Procedure
2,4-dichloro-5-(trifluoromethyl)pyridine (800 mg, 3.70 mmol), 2,6-dimethylpiperazine (800 mg, 7.14 mmol), and K2CO3 (1.0 g, 7.25 mmol) were added to dimethylformamide (15 mL). The resulting solution was heated for 2 h at 140° C. The reaction mixture was then quenched by the adding 50 mL of ice-water and extracted with EtOAc (50 mL). The organic layers were combined and dried over MgSO4. The solvent was concentrated and the residue was purified using silica gel column chromatography to 0.2 g (18%) of 1-(4-chloro-5-(trifluoromethyl)pyridine-2-yl)-cis-3,5-dimethylpiperazine.
Workup
- customThe reaction mixture was then quenched by the adding 50 mL of ice-water
- extractionextracted with EtOAc (50 mL)
- dry with materialdried over MgSO4
- concentrationThe solvent was concentrated
- customthe residue was purified
Sources & evidence
- ORD record
- ord-41598333c8324828b1a669ce03e1444d
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07494999B2
Reaction notes
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