p-Fluoronitrobenzene → 1-Benzyl-3-(4-nitrophenoxy)piperidine

HRID 1711419Notes

Reaction equation

HRID 1711419 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[H-].[Na+]>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 857731-Benzylpiperidin-3-ol

Product 1

HCID 222600571-Benzyl-3-(4-nitrophenoxy)piperidineYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-benzyl-3-hydroxypiperidine (2.0 g, 10 mmoles), p-fluoro-nitrobenzene (1.06 ml, 12 mmoles) and sodium hydride (0.285 g, 12 mmoles) in DMF was stirred at room temperature for 3 hours, diluted with H2O and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by flash chromatography using as eluent 50% EtOAc/hexane to afford the title compound (3.0 g, 9.43 mmoles).

Workup

  1. extractionextracted with EtOAc
  2. washwashed sequentially with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-29965b3b47f0445f9b56d55f20facd7c
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

Loading…