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

HRID 640998Notes

Reaction equation

HRID 640998 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-312e8b9d608149058b3b61491211c47e
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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