p-Fluoronitrobenzene → HCID 49760192, compound

HRID 1429230Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[Al]>O.CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:20]2[CH2:21][CH2:22][CH:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18][CH2:19]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 190 °C

Procedure

An oven-dried 20 mL microwave tube was charged with 4-fluoronitrobenzene (0.752 mL, 7.02 mmol), 4-phenylpiperidine (1.166 g, 7.02 mmol), and potassium carbonate (0.970 g, 7.02 mmol) under nitrogen, anhydrous DMSO (7 mL) was added, the tube was sealed with an aluminum crimp cap, and heated in a microwave reactor (Personal Chemistry, 300 W, 2.4 bar) at 190° C. for 10 minutes. TLC (SiO2, 5% EtOAc/hexanes) showed complete reaction. The reaction was poured into water (50 mL), stirred for 5 minutes, and vacuum filtered in a Büchner funnel. The collected yellow solids were washed with water (2×10 mL) and Et2O (5 mL), and the bright yellow solid was dried in vacuo to provide the title compound (1.712 g, 6.06 mmol, 86%). 1H NMR (400 MHz, CDCl3) δ ppm 1.73-1.90 (m, 2 H), 2.00 (d, J=13.34 Hz, 2 H), 2.73-2.86 (m, 1 H), 3.02-3.17 (m, 2 H), 4.10 (d, J=13.23 Hz, 2 H), 6.87 (d, J=9.43 Hz, 2 H), 7.23 (t, J=7.75 Hz, 3 H), 7.33 (t, J=7.43 Hz, 2 H), 8.14 (d, J=9.33 Hz, 2 H); MS (ESI+) m/z 283 (M+H)+.

Workup

customreaction
filtrationvacuum filtered in a Büchner funnel
washThe collected yellow solids were washed with water (2×10 mL) and Et2O (5 mL)
customthe bright yellow solid was dried in vacuo

Sources & evidence

ORD record: ord-2cea4df430804df4b0655e2a4e9407e0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937150B2

Reaction notes

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