Toluene → HCID 86695293, compound

HRID 1410549Notes

Reaction equation

HRID 1410549 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][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:18]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][C:8]2([O:11][CH2:18]2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 10899796HCID 10899796, compound

Product 1

HCID 86695293HCID 86695293, compound

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
80 °C

Procedure

68.95 g (0.333 mol) of 1-(2-fluorobenzyl)-4-piperidone crude product was added to a reaction bottle, and 290 mL of toluene was added. The reaction heated at 80° C. in an oil bath under stirring, and then to the reaction 83.00 g (0.377 mol) of trimethylsulfoxide iodide and 2.20 g (0.0065 mol) of tetrabutylammonium hydrogen sulfate was added in sequence. Then to the reaction 28.40 g (0.710 mol) sodium hydroxide dissolved in 90 mL of aqueous solution was added dropwise under stirring. After the addition, the reaction was stirred at 80° C. of bath temperature overnight. On the next day, the reaction was cooled, washed with water twice, extracted with a small amount of toluene, combined, and the solvent was recovered to obtain light yellow liquid, 54.70 g (74.2%), i.e., a crude target product. 1H-NMR (CDCl3, ppm) δ: 7.394 (1H, dt, J1=7.56 Hz, J2=1.68 Hz), 7.254 (1H, m), 7.118 (1H, ddd, J1=7.56 Hz, J2=1.12 Hz), 7.037 (1H, dtd, J1=8.96 Hz, J2=1.12 Hz), 3.562 (2H, d, J=1.12 Hz), 2.647 (2H, s), 2.637 (4H, m), 1.820 (2H, m), 1.569 (2H, m).

Workup

  1. additionwas added
  2. additionwas added in sequence
  3. additionwas added dropwise
  4. stirringunder stirring
  5. additionAfter the addition
  6. stirringthe reaction was stirred at 80° C. of bath temperature overnight
  7. temperatureOn the next day, the reaction was cooled
  8. washwashed with water twice
  9. extractionextracted with a small amount of toluene
  10. customthe solvent was recovered
  11. customto obtain light yellow liquid, 54.70 g (74.2%), i.e.

Sources & evidence

ORD record
ord-cbf82e1c463146768f42389a2d43fb59
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

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