Sodium Iodide → HCID 57430094, compound

HRID 852284Notes

Reaction equation

HRID 852284 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[C:10](=[O:13])([O-])[O-:11].[K+].[K+].S([C:20]1[CH:26]=[CH:25]C(C)=[CH:22][CH:21]=1)([O-])(=O)=O.[I-].[Na+]>C(#N)C>[O:11]1[CH2:22][CH2:21][CH:20]([CH2:26][CH2:25][N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[O:13][CH2:10]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 2723901Piperonylamine

Product 1

HCID 57430094HCID 57430094, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-piperidone monohydrate hydrochloride (1.26 g, 8.23 mmol) in acetonitrile (100 mL), potassium carbonate (3.4 g, 24.6 mmol) was added, followed by the tosylate 128NLS46-B (3.54 g, 12.36 mmol) and sodium iodide (1.85 g, 12.35 mmol) and stirring was continued overnight at 60° C. The mixture was filtered, the filtrate evaporated in vacuo and the residue partitioned between 1M NaOH and ethyl acetate. The organic layer was separated, the aqueous layer extracted twice with ethyl acetate and the combined organic layers dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 0–4% methanol in dichloromethane, afforded 1-[2-(1,3-dioxan-4-yl)ethyl]piperidin-4-one (128NLS50, 1.73 g, 98%).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. customthe residue partitioned between 1M NaOH and ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted twice with ethyl acetate
  7. dry with materialthe combined organic layers dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customPurification of the residue by silica gel column chromatography
  11. washeluting with a stepwise gradient of 0–4% methanol in dichloromethane

Sources & evidence

ORD record
ord-e53549603fea4d88842bc8016b0f4a64
Source dataset
uspto-grants-2007_08
Patent number
US07253186B2

Reaction notes

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