Benzenesulfonic Acid → HCID 19772019, compound

HRID 1614624Notes

Reaction equation

HRID 1614624 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C1(S(O)(=O)=O)C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1(C)C(C)=CC=CC=1.C1COCC1.O>[OH2:10].[ClH:1].[ClH:1].[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[CH:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[CH:23][CH:22]=1

Participants

9

Reactant 5

HCID 7371Benzenesulfonic AcidHCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 19772107HCID 19772107, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19772019HCID 19772019, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 29.36 g (0.103 mol) of (4-fluorophenyl)[1-(1-methylethyl)-4-piperidinyl]methanone hydrochloride, 28.9 g (0.260 mol) of 4-fluoroaniline and 0.61 g (3.9 mmol) of benzenesulfonic acid in 500 mL of xylene was heated at reflux for 20 h. Water was removed with a Dean-Stark trap. The solvent was removed in vacuo. The residue was reacted with 6.0 g (0.16 mol) of LiAlH4 in 400 mL of THF at room temperature. After 23 h, dilute NaOH and then water were added slowly. The mixture was filtered through Celite®, and CH2Cl2 (400 mL) was added to the filtrate. The mixture was extracted with several portions of water and was dried (Na2SO4). The solvent was removed in vacuo. The residue was dissolved in CH3OH and treated with an excess of ethereal HCl. The hydrochloride salt was collected to give 13.8 g (32.1%) of the title compound as a white solid, mp 225°-228° C. An additional 4.58 g (10.2%) of product was collected from the filtrate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customWater was removed with a Dean-Stark trap
  4. customThe solvent was removed in vacuo
  5. filtrationThe mixture was filtered through Celite®, and CH2Cl2 (400 mL)
  6. additionwas added to the filtrate
  7. extractionThe mixture was extracted with several portions of water
  8. dry with materialwas dried (Na2SO4)
  9. customThe solvent was removed in vacuo
  10. dissolutionThe residue was dissolved in CH3OH
  11. additiontreated with an excess of ethereal HCl
  12. customThe hydrochloride salt was collected

Sources & evidence

ORD record
ord-42539fc1085745abade96da052e71fe5
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

Loading…