Potassium Iodide → 1-(2-(3-Fluoro-4-nitrophenoxy)ethyl)piperidine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CCOC(C)=O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 3-fluoro-4-nitrophenol (3.07 g, 19.54 mmol), 1-(2-chloroethyl)piperidine hydrochloride (3.60 g, 19.54 mmol), cesium carbonate (19.10 g, 58.6 mmol) and potassium iodide (1.622 g, 9.77 mmol) were combined with DMF (19.54 mL), and the mixture was heated at 50° C. for 36 hours. The resulting mixture was diluted with EtOAc (50 mL), washed with water (100 mL) and the water layer extracted with EtOAc (30 mL). The combined organic layers were washed with water (20 mL×2), 1N aqueous NaOH, and brine, and the organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified via flash chromatography using a linear gradient of 0% to 5% of 1% NH4OH in MeOH in DCM. The title compound was isolated as a yellow liquid (662 mg, 13% yield).
Workup
- washwashed with water (100 mL)
- extractionthe water layer extracted with EtOAc (30 mL)
- washThe combined organic layers were washed with water (20 mL×2), 1N aqueous NaOH, and brine
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
- customThe residue was purified via flash chromatography
Sources & evidence
- ORD record
- ord-c6c5f94887d846b78e49d77e8361971e
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115127B2
Reaction notes
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