Benzenesulfonic Acid → HCID 19771943, compound

HRID 1614642Notes

Reaction equation

HRID 1614642 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15](=O)[C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10][CH2:11]2)=[N:30][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 673264-FluorobenzylamineHCID 10470715HCID 10470715, compound

Product 1

HCID 19771943HCID 19771943, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 11.4 g (0.037 mol) of N-(2-phenylethyl)-4-(4-fluorobenzoyl)piperidine, 6.79 g (0.054 mol) of 4-fluorobenzylamine and 0.54 g (0.0034 mol) of benzenesulfonic acid in 400 mL of xylene was heated at reflux for 24 h. Water was removed from the reaction mixture with a Dean-Stark trap. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo to give 12.46 g (81.2%) a-(4-fluorophenyl)-N-[(4-fluorophenyl)methyl]-1-(2-phenylethyl)-4-piperidinemethanimine as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  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 (Na2SO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4f78dc38877f4e6da9a705925136d3c1
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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