Potassium Carbonate → (2-Nitrophenyl)(tetrahydropyran-3-yl)amine
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH2:7])[CH2:2]1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:7][CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)([O-:17])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
A solution of tetrahydropyran-3-ylamine (0.43 g, 4.05 mmol) in DMF (2 mL) was added to a mixture of 1-fluoro-2-nitrobenzene (0.57 g, 4.05 mmol) and potassium carbonate (1.68 g, 12.1 mmol) in DMF (10 mL). The reaction mixture was heated for 1 h at 135° C. under microwave irradiation. Additional tetrahydropyran-3-ylamine (40 mg) was added and microwave irradiation at 135° C. was continued for further 30 min. Volatiles were then removed in vacuo and the resulting residue was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM) affording (2-Nitrophenyl)(tetrahydropyran-3-yl)amine as an orange oil (0.73 g, 81%). LCMS: RT 3.31 min [M+H]+ 223.2.
Workup
- custommicrowave irradiation at 135° C.
- customVolatiles were then removed in vacuo
- customthe resulting residue was partitioned between EtOAc and water
- extractionThe aqueous phase was further extracted with EtOAc (×2)
- washthe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% MeOH in DCM)
Sources & evidence
- ORD record
- ord-32157efcf13e45fcb64b10a7eedaa300
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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