1-Fluoro-2-nitrobenzene → 1-(4-Nitrophenyl)-4-piperidinol

HRID 2352930Notes

Reaction equation

HRID 2352930 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[N+:8]([C:3]1[CH:4]=[CH:5][C:6]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:2]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 79341Piperidin-4-olHCID 81531Diisopropylethylamine

Product 1

HCID 6137681-(4-Nitrophenyl)-4-piperidinolYield 145.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 100 mL round bottom flask was dried in an oven overnight and cooled to room temperature under Ar(g). The flask was charged with fluoronitrobenzene (0.500 mL, 4.71 mmol), Piperidin-4-ol (0.619 g, 2.30 mmol) and dioxane (9.0 mL). To the resulting solution, diisopropyl ethyl amine (0.463 mL, 6.12 mmol) was added dropwise, and the reaction was allowed to stir at 105° C. for 48 h. The mixture was extracted with EtOAc (3ט50 mL), and brine (2ט50 mL). The combined organic layers were then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude mixture was then purified over silica (10% MeOH/90% CHCl3) affording a yellow solid (0.742 g, 3.34 mmol, 71% yield).

Workup

  1. customA 100 mL round bottom flask was dried in an oven overnight
  2. extractionThe mixture was extracted with EtOAc (3ט50 mL), and brine (2ט50 mL)
  3. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was then purified over silica (10% MeOH/90% CHCl3)

Sources & evidence

ORD record
ord-e6009f6828af4b2188a5970cd11b92ac
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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