Sodium Iodide → n-[1-(p-Nitrophenethyl)-4-piperidinyl]-n-phenylpropionamide

HRID 2215642Notes

Reaction equation

HRID 2215642 reaction equation
[CH3:1][CH2:2][C:3]([N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:4].[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26]Br)=[CH:23][CH:22]=1)([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)CC(=O)C>[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][CH2:26][N:9]2[CH2:8][CH2:7][CH:6]([N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:3](=[O:4])[CH2:2][CH3:1])[CH2:11][CH2:10]2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 2593814-(N-Propionylaniline)piperidine

Product 1

HCID 13408923n-[1-(p-Nitrophenethyl)-4-piperidinyl]-n-phenylpropionamideYield 56%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A suspension of norfentanyl of Example 4 (6.71 g, 0.029 mol), p-nitrophenethylbromide (7.178 g, 0.0372 mol), potassium carbonate (19 g, 0.14 mol) and a few crystals of sodium iodide in 4-methyl-2-pentanone (200 ml) was stirred overnight at reflux, under nitrogen. After cooling to room temperature, the precipitate was removed by filtration and the solution concentrated under reduced pressure. The dark residue was dissolved in ethyl acetate (200 ml) and washed with water (2×100 ml), dried over sodium sulfate, filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica gel, 10% MeOH/90% CHCl3 v/v) to give the title compound as a yellow solid (5.33 g, 56% yield).

Workup

  1. temperatureat reflux, under nitrogen
  2. customthe precipitate was removed by filtration
  3. concentrationthe solution concentrated under reduced pressure
  4. dissolutionThe dark residue was dissolved in ethyl acetate (200 ml)
  5. washwashed with water (2×100 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by column chromatography (silica gel, 10% MeOH/90% CHCl3 v/v)

Sources & evidence

ORD record
ord-f5ba4c2185494aaba25de8ea0744f985
Source dataset
uspto-grants-2006_09
Patent number
US07109310B2

Reaction notes

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