Toluene → HCID 86695294, compound

HRID 1410550Notes

Reaction equation

HRID 1410550 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].[C:18]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][C:10]3([O:13][CH2:18]3)[CH2:11][CH2:12]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 11959533HCID 11959533, compound

Product 1

HCID 86695294HCID 86695294, compound

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
80 °C

Procedure

61.00 g (0.295 mol) of 1-(4-fluorobenzyl)-4-piperidone crude product was added to a reaction bottle, to which 260 mL of toluene was added. The reaction was heated and stirred at 80° C. in an oil bath, and to the reaction 70.00 g (0.318 mol) of trimethylsulfoxide iodide and 2.70 g (0.0080 mol) of tetrabutylammonium hydrogen sulfate were added in sequence, then 28.00 g (0.700 mol) sodium hydroxide dissolved in 120 mL of aqueous solution was added dropwise under stirring. After the addition, the reaction was continuously stirred at 80° C. bath temperature 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, 47.50 g (72.8%), i.e., a crude target product, 1H-NMR (CDCl3, ppm) δ: 7.298 (2H, m), 7.007 (2H, m), 3.519 (2H, s), 2.565 (2H, s), 2.559 (4H, m), 1.827 (2H, m), 1.534 (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 80° C. bath temperature 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
  13. customto obtain light yellow liquid, 47.50 g (72.8%), i.e.

Sources & evidence

ORD record
ord-0b70b13b7ed94abca587b66231ba2716
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

Loading…