Sodium hydride → 4-(3,4-Dinitrophenoxy)-1-methylpiperidine

HRID 1012085Notes

Reaction equation

HRID 1012085 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.[H-].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 2986753,4-Dinitrofluorobenzene

Product 1

HCID 714182034-(3,4-Dinitrophenoxy)-1-methylpiperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dinitrofluorobenzene (1.86 g, 10 mmol) and 4-hydroxy-1-methylpiperidine (1.38 g, 12 mmol) were dissolved in THF (20 ml) and stirred at ambient temperature while sodium hydride (60% dispersion in mineral oil, 0.40 g, 10 mmol) was added in several small portions. The reaction mixture was stirred for one hour and then reduced in vacuo, partitioned between ethyl acetate and water, and the organic phase washed with brine, dried (MgSO4) and reduced in vacuo. The resulting residue was subject to column chromatography, eluting with 5% MeOH/DCM to give a yellow solid (1.76 g, 2:1 ratio of desired 4-(3,4-dinitro-phenoxy)-1-methyl-piperidine and a side product, 4-(4-fluoro-2-nitro-phenoxy)-1-methyl-piperidine).

Workup

  1. additionwas added in several small portions
  2. custompartitioned between ethyl acetate and water
  3. washthe organic phase washed with brine
  4. dry with materialdried (MgSO4)
  5. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-10192f4806dd4d578f64378b4ef4f49a
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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