p-Fluoronitrobenzene → 1-(4-nitrophenyl)piperidin-3-ol

HRID 2409882Notes

Reaction equation

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

Participants

Reactant 2

HCID 9590p-Fluoronitrobenzene

HCID 232933-Hydroxypiperidine

Product 1

HCID 44174281-(4-nitrophenyl)piperidin-3-ol

Procedure

1-(4-Nitrophenyl)piperidin-3-ol was synthesized as described in General Procedure A using 1-fluoro-4-nitrobenzene (4.41 g, 31.2 mmol) and piperidin-3-ol (4.3 g, 31.2 mmol) to give an orange solid (6.8 g, 30.6 mmol, 98% yield). Anal. Calcd. for C11H14N2O3 m/z 222.2, found: 223.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.14-7.98 (m, 2 H), 6.83 (d, J=9.35 Hz, 2 H), 3.89 (d, J=3.85 Hz, 1 H), 3.72 (dd, J=12.92, 3.57 Hz, 1 H), 3.53 (ddd, J=13.06, 5.91, 3.02 Hz, 1 H), 3.33-3.16 (m, 2 H), 2.10-1.97 (m, 2 H), 1.96-1.84 (m, 1 H), 1.75-1.50 (m, 2 H).

Sources & evidence

ORD record: ord-600b02f7a41e4cb6b46ce9e8e84cde5d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815909B2

Reaction notes

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