p-Toluenesulfonic acid → HCID 11624255, compound

HRID 2235268Notes

Reaction equation

HRID 2235268 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[C:6]1=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)[C:6]1=[O:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59299318HCID 59299318, compound

Product 1

HCID 11624255HCID 11624255, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one (14.56 g, 37.90 mmol) in acetone (400 mL) with stirring at room temperature. Add p-toluene sulfonic acid (6.53 g, 37.90 mmol) and stir the reaction at room temperature for 48 hours. Then add water and extract the aqueous layer with ethyl acetate (3×400 mL). Combine the organic layers and dry with Na2SO4. Filter and concentrate to give 12.95 g (100%) of the crude title compound as a white solid: Mass spectrum (ion spray): m/z=340.1, 342.0 (M+1).

Workup

  1. customthe reaction at room temperature for 48 hours
  2. extractionThen add water and extract the aqueous layer with ethyl acetate (3×400 mL)
  3. dry with materialCombine the organic layers and dry with Na2SO4
  4. filtrationFilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-2909f9cfcac34ffe934d3d8bee368570
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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