Sodium Carbonate → 1-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethyl]piperidin-4-one

HRID 65956Notes

Reaction equation

HRID 65956 reaction equation
S(O[CH2:12][CH2:13][CH:14]1[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]1)(C1C=CC(C)=CC=1)(=O)=O.Cl.[NH:25]1[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:31]=[C:28]1[CH2:29][CH2:30][N:25]([CH2:12][CH2:13][CH:14]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][CH2:15]2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 30848514-Piperidone hydrochlorideHCID 128505822-(2-Tosyloxyethyl)-1,4-benzodioxan

Product 1

HCID 205401701-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethyl]piperidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The starting material is prepared as follows: The mixture of 10 g of 2-(2-tosyloxyethyl)-1,4-benzodioxan, 10 g of 4-piperidone hydrochloride, 20 g of anhydrous sodium carbonate and 160 ml of dimethylformamide is stirred vigorously at room temperature for 48 hours. It is filtered, the residue washed with a small amount of dimethylformamide and the filtrate evaporated. The residue is dissolved in ethyl acetate, the solution extracted with hydrochloric acid, the extract made alkaline with 50% aqueous sodium hydroxide while cooling and re-extracted with methylene chloride. The latter extract is dried and evaporated, to yield the 2-[2-(4-oxopiperidino)-ethyl]-1,4-benzodioxan, which solidifies on standing.

Workup

  1. customThe starting material is prepared
  2. filtrationIt is filtered
  3. washthe residue washed with a small amount of dimethylformamide
  4. customthe filtrate evaporated
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. extractionthe solution extracted with hydrochloric acid
  7. temperaturewhile cooling
  8. extractionre-extracted with methylene chloride
  9. extractionThe latter extract
  10. customis dried
  11. customevaporated

Sources & evidence

ORD record
ord-fa7bf53de7d946db865479a55c23dbed
Source dataset
uspto-grants-1978_12
Patent number
US04129655

Reaction notes

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