Piperidine → 1-{2-[2-Fluoro-5-(methyloxy)-4-nitrophenyl]ethyl}piperidine

HRID 419450Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[C:6]([F:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CC(O)C>[F:11][C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][CH2:10][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 180 °C

Procedure

To 5-ethenyl-4-fluoro-2-nitrophenyl methyl ether (1.0 g, 5.1 mmol) in 10 mL of iPrOH was added, piperidine (1.3 g, 15.2 mmol). The mixture was heated to 180° C. 17 min in the microwave. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step C (0.81 g, 2.87 mmol, 57%). 1H NMR (400 MHz, CDCl3) δ ppm 7.59 (d, J=8.97 Hz, 1H), 7.01 (d, J=5.86 Hz, 1H), 3.92 (s, 3H), 2.82-2.88 (m, 2H), 2.53-2.58 (m, 2H), 2.40-2.48 (m, 4H), 1.55-1.61 (m, J=5.49, 5.49, 5.49, 5.49 Hz, 4H), 1.40-1.47 (m, 2H).

Workup

custom17 min
customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-a73dc098bef64953b5c0ae0f25e85840
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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