Water → 4-(4-Fluorobenzoylamino)-1-methylsulfonylpiperidine

HRID 49786Notes

Reaction equation

HRID 49786 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>ClCCl>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([S:24]([CH3:23])(=[O:26])=[O:25])[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 1

HCID 50099994-(4-Fluorobenzoylamino)-1-methylsulfonylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-fluorobenzoylamino)piperidine (0.15 g) in dichloromethane (5 ml) were added in turn pyridine (0.14 ml) and methanesulfonyl chloride (96 μl) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour. To the mixture was added N,N-dimethylaminopyridine (0.13 g) and allowed to stir for another 1 hour. The reaction mixture was taken up into a mixture of water and dichloromethane. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give 4-(4-fluorobenzoylamino)-1-methylsulfonylpiperidine (0.30 g).

Workup

  1. stirringto stir for another 1 hour
  2. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation under reduced pressure
  5. customgave a residue, which
  6. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-2f51fc0c5b304c23b768fa1289a84422
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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