Trifluoroacetic acid → HCID 28952599, compound
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH:12]1[CH2:11][CH2:10][CH:9]([C:4]2[C:3]([C:2]([F:23])([F:1])[F:22])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13]1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(3-(trifluoromethyl)pyridin-2-yl)piperidine-1-carboxylate (379.8 mg, 1.10 mmol, 1.00 equiv, 96%) in dichloromethane (10 mL). This was followed by the addition of trifluoroacetic acid (5 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 3 h at room temperature. The pH value of the solution was adjusted to 8-9 with sat sodium bicarbonate. The resulting solution was extracted with 6×50 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 237.4 mg (93%) of 2-(piperidin-4-yl)-3-(trifluoromethyl)pyridine as yellow oil.
Workup
- customInto a 50-mL round-bottom flask, was placed
- stirringThe resulting solution was stirred for 3 h at room temperature
- extractionThe resulting solution was extracted with 6×50 mL of dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe solids were filtered out
- concentrationThe resulting mixture was concentrated under vacuum
- customThis resulted in 237.4 mg (93%) of 2-(piperidin-4-yl)-3-(trifluoromethyl)pyridine as yellow oil
Sources & evidence
- ORD record
- ord-fc86821a06b54c35b09a0668a75dd3d4
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916560B2
Reaction notes
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