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

HRID 876348Notes

Reaction equation

HRID 876348 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1[C:22]2([CH2:27][CH2:26][N:25]([C:28]([N:30]3[CH2:35][CH:34]([C:36]4[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=4)[CH2:33][CH:32]([NH:46][C:47]([CH:49]4[CH2:53][CH2:52][CH2:51][CH2:50]4)=[O:48])[CH2:31]3)=[O:29])[CH2:24][CH2:23]2)[O:21]CC1>CC(C)=O.O>[O:21]=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([N:30]2[CH2:35][CH:34]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:38][CH:37]=3)[CH2:33][CH:32]([NH:46][C:47]([CH:49]3[CH2:53][CH2:52][CH2:51][CH2:50]3)=[O:48])[CH2:31]2)=[O:29])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 66701500N-{1-(1,4-Dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}-cyclopentanecarboxamide

Product 1

HCID 46931417N-{1-[(4-Oxopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}cyclopentanecarboxamide

Reagents, catalysts & solvents 1

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

Procedure

14.3 mg of pyridinium p-toluenesulphonate (0.057 mmol) were added to a solution of the acetal from Example 63A (97.2 mg, 0.191 mmol) in 5.5 ml of acetone/water (10:1), and the mixture was stirred under reflux overnight. Another 14.3 mg of pyridinium p-toluenesulphonate (0.057 mmol) were added, and the mixture was stirred under reflux for another night. The mixture was then cooled, and the precipitate formed was filtered off. Yield: 66.2 mg (74% of theory)

Workup

  1. temperatureunder reflux overnight
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for another night
  4. temperatureThe mixture was then cooled
  5. customthe precipitate formed
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-d68b0c0211f545a48670a6127fbec740
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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