Benzenesulfonic Acid → HCID 19772094, compound

HRID 1614623Notes

Reaction equation

HRID 1614623 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](=O)[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH2:11][CH2:12]2)=[N:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 7504BenzylamineHCID 1438176HCID 1438176, compound

Product 1

HCID 19772094HCID 19772094, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.32 g (0.0297 mol) of N-benzenesulfonyl-4-(p-fluorobenzoyl)piperidine, 5.4 g (0.0505 mol) of benzylamine and 0.5 g (0.0032 mol) of benzenesulfonic acid in 500 mL of toluene was heated at reflux. Water was removed from the reaction mixture with a Dean-Stark trap. After 134.5 h, the solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (MgSO4), the volume was reduced to 100 mL, and 200 mL of ether was added. A precipitate was collected to give 10.0 g (77.1%) of the title compound as a white crystalline solid, mp 153°-155°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customWater was removed from the reaction mixture 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 solution was dried (MgSO4)
  7. additionwas added
  8. customA precipitate was collected

Sources & evidence

ORD record
ord-e6447f00db9540d8bcca279be6eed8c8
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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