Sodium Iodide → 1-[4-(3-Piperidin-1-ylpropoxy)phenyl]ethanone

HRID 887051Notes

Reaction equation

HRID 887051 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Cl.Cl[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[NH3:16].[N:16]1([CH2:15][CH2:14][CH2:13][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 2

HCID 222AmmoniaHCID 22001121-[4-(3-Piperidin-1-ylpropoxy)phenyl]ethanoneYield 6.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.97 g of 4′-hydroxyacetophenone (43.8 mmol), 13.0 g of 1-(3-chloropropyl)-piperidine hydrochloride (65.8 mmol), 12.70 g of potassium carbonate (91.89 mmol), and 3.28 g of sodium iodide (21.9 mmol) in 100 mL dry acetone was stirred at reflux. After 1.5 h, the reaction was cooled to room temperature, filtered and concentrated. Ethyl acetate was added and the white solid that remained was filtered off. The filtrate was concentrated in vacuo and the crude residue was purified via silica gel chromatography using a gradient of ethyl acetate then 400:20:10 ethyl acetate: 7N ammonia in methanol:methanol to yield 583 mg of 1-[4-(3-piperidin-1-ylpropoxy)phenyl]ethanone as an oil. MS m/z 265 (M+H).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionEthyl acetate was added
  5. filtrationthe white solid that remained was filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe crude residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-766088a8d3ac45c2a49b4edb14c80823
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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