Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-Chloro-N-{1-[(4-oxopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876349Notes

Reaction equation

HRID 876349 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]([NH:27][CH:28]2[CH2:33][CH:32]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)[CH2:31][N:30]([C:44]([N:46]3[CH2:55][CH2:54][C:49]4(OCC[O:50]4)[CH2:48][CH2:47]3)=[O:45])[CH2:29]2)=[O:26])[CH:22]=[CH:23][CH:24]=1>CC(C)=O.O>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]([NH:27][CH:28]2[CH2:33][CH:32]([C:34]3[CH:35]=[CH:36][C:37]([C:40]([F:42])([F:41])[F:43])=[CH:38][CH:39]=3)[CH2:31][N:30]([C:44]([N:46]3[CH2:47][CH2:48][C:49](=[O:50])[CH2:54][CH2:55]3)=[O:45])[CH2:29]2)=[O:26])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 667610613-Chloro-N-{1-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Product 1

HCID 469314193-Chloro-N-{1-[(4-oxopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

54.6 mg of pyridinium p-toluenesulphonate (0.217 mmol) were added to a solution of the acetal from Example 64A (400 mg, 0.725 mmol) in 15 ml of acetone/water (10:1) and the mixture was stirred under reflux for 3 d, with another 54.6 mg of pyridinium p-toluenesulphonate (0.217 mmol) being added after 24 h and 48 h. The solvent was then removed under reduced pressure, the residue was taken up in water and the mixture was extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 363 mg (92% of theory)

Workup

  1. additionbeing added after 24 h and 48 h
  2. customThe solvent was then removed under reduced pressure
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a679c2ea003b49278c865797eb195001
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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