Benzenesulfonic Acid → HCID 19772064, compound

HRID 1614602Notes

Reaction equation

HRID 1614602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=O)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[F:25][C:26]1[CH:32]=[CH:31][C:29]([N:30]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 97314-FluoroanilineHCID 1438176HCID 1438176, compound

Product 1

HCID 19772064HCID 19772064, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 13.0 g (0.037 mol) of (4-fluorophenyl)[1-(phenylsulfonyl)-4-piperidinyl]methanone, 24.4 g (0.22 mol) of 4-fluoroaniline, and 0.7 g (0.004 mol) of benzenesulfonic acid in 500 mL of xylene was heated at reflux for 7 days. Water was removed with a Dean-Stark trap. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 phase was dried (Na2SO4), and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2 /hexane to give 11.24 g (69%) of a light grey solid, mp 123°-124° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 days
  3. customWater was removed with a Dean-Stark trap
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  6. dry with materialThe CH2Cl2 phase was dried (Na2SO4)
  7. customthe solvent was removed in vacuo
  8. customThe residue was recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-9128bdc5f0684467b654627458d13a49
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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