Potassium Carbonate → HCID 43610331, compound

HRID 242824Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][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:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 135 °C

Procedure

A solution of tetrahydropyran-4-ylamine (0.75 g, 7.44 mmol) in DMF (2 mL) was added to a mixture of 1-fluoro-2-nitrobenzene (1.00 g, 7.09 mmol) and potassium carbonate (2.94 g, 21.3 mmol) in DMF (10 mL). The reaction mixture was heated for 1 h at 135° C. under microwave irradiation and then volatiles were removed in vacuo. 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 affording (2-Nitrophenyl)(tetrahydropyran-4-yl)amine as a yellow solid (1.58 g, quantitative). 1H NMR (CDCl3, 400 MHz): δ 8.18 (1H, d, J=8.65 Hz), 8.09 (1H, s), 7.42 (1H, t, J=7.81 Hz), 6.87 (1H, d, J=8.70 Hz), 6.64 (1H, t, J=7.72), 4.06-3.98 (2H, m), 3.79-3.68 (1H, m), 3.57 (2H, t, J=11.32 Hz), 2.14-2.01 (2H, m), 1.74-1.61 (2H, m).

Workup

customvolatiles were 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

Sources & evidence

ORD record: ord-027b46e9bc07454c8a1a016c23f44954
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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