Toluene → HCID 86695295, compound

HRID 1410552Notes

Reaction equation

HRID 1410552 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1.[OH-].[Na+].[C:19]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([O:11][CH2:19]2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 11959582HCID 11959582, compound

Product 1

HCID 86695295HCID 86695295, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
80 °C

Procedure

28.20 g (0.125 mol) of 1-(2,4-difluorobenzyl)-4-piperidone crude product was added to a reaction bottle, to which 200 mL of toluene was added. The reaction was heated and stirred at 80° C. in an oil bath, and to the reaction 29.60 g (0.135 mol) of trimethylsulfoxide iodide and 0.60 g (0.0018 mol) of tetrabutylammonium hydrogen sulfate were added in sequence and then 11.40 g (0.285 mol) of sodium hydroxide dissolved in 60 mL of aqueous solution was added dropwise under stirring. After the addition, the reaction was continuously stirred at bath temperature of 80° C. overnight. On the next day, the reaction was cooled, washed with water twice, extracted with a small amount of toluene, combined and dried, and the solvent was recovered to obtain light yellow liquid 22.00 g (73.6%), i.e., a crude target product, 1H-NMR (CDCl3, ppm) δ: 7.361 (1H, m), 6.76-6.89 (2H, m), 3.597 (2H, d, J=1.12 Hz), 2.651 (2H, s), 2.601 (4H, m), 1.829 (2H, m), 1.545 (2H, m).

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. additionwere added in sequence
  4. additionwas added dropwise
  5. stirringunder stirring
  6. additionAfter the addition
  7. stirringthe reaction was continuously stirred at bath temperature of 80° C. overnight
  8. temperatureOn the next day, the reaction was cooled
  9. washwashed with water twice
  10. extractionextracted with a small amount of toluene
  11. customdried
  12. customthe solvent was recovered

Sources & evidence

ORD record
ord-d70e6a3016fa4a53bf850b1119fa47a4
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

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