Sodium Carbonate → HCID 57430097, compound

HRID 852289Notes

Reaction equation

HRID 852289 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.O.[NH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1.Br[CH2:17][CH2:18][CH:19]1[O:24][CH2:23][CH2:22][CH2:21][O:20]1>C(#N)C>[O:20]1[CH2:21][CH2:22][CH2:23][O:24][CH:19]1[CH2:18][CH2:17][N:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-HCID 2723901Piperonylamine

Product 1

HCID 57430097HCID 57430097, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Sodium carbonate (17.4 g, 125.9 mmol) was added to a solution of 4-piperidone monohydrate hydrochloride (6.45 g, 42.0 mmol) in acetonitrile (200 mL). After 30 minutes stirring at rt a solution of 2-(2-bromoethyl)-1,3-dioxane (8.45 g, 43.3 mmol) in acetonitrile (50 mL) was added dropwise to the reaction mixture and stirring was continued overnight at rt and at reflux for an additional 2 hours. The solvent was removed by evaporation under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with 7% methanol in dichloromethane, afforded 1-[2-(1,3-dioxan-2-yl)ethyl]piperidin-4-one (6.19 g, 69%).

Workup

  1. additionwas added dropwise to the reaction mixture
  2. temperatureat reflux for an additional 2 hours
  3. customThe solvent was removed by evaporation under reduced pressure
  4. customthe residue was partitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification of the residue by silica gel column chromatography
  9. washeluting with 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-8b40d3cd297b48559f1d81ff8cb4bf8d
Source dataset
uspto-grants-2007_08
Patent number
US07253186B2

Reaction notes

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