Benzenesulfonic Acid → HCID 19772006, compound

HRID 1614603Notes

Reaction equation

HRID 1614603 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:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.C1(S(O)(=O)=O)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[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)=[N:31][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 673264-FluorobenzylamineHCID 1438176HCID 1438176, compound

Product 1

HCID 19772006HCID 19772006, compoundYield 63.68%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 22.26 g (0.064 mol) of (4-fluorophenyl)[1-(phenylsulfonyl)-4-piperidinyl]methanone, 12.51 g (0.10 mol) of 4-fluorobenzylamine, and 0.76 g (0.0048 mol) of benzenesulfonic acid in 400 mL of xylene was heated at reflux for 25.5 h. 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 solution was dried (Na2SO4), and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2 -hexane to give 18.49 g (63.68%) of white crystalline solid, mp 114°-116° C. A second crop of 3.27 g (11.28%) of product was isolated from the filtrate as a white solid, mp 110°-112° C.

Workup

  1. temperatureat reflux for 25.5 h
  2. customWater was removed with a Dean-Stark trap
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CH2Cl2 and dilute NaOH
  5. dry with materialThe CH2Cl2 solution was dried (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customThe residue was recrystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-084b9c10378c4221964a74d4bcf4fbf9
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

Loading…