Water → 1-Tosylpiperidin-4-one

HRID 2093077Notes

Reaction equation

HRID 2093077 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.N1C=CC=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[OH2:26]>ClCCl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:2]2[CH2:7][CH2:6][C:5](=[O:26])[CH2:4][CH2:3]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 20088740Piperidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 5609571-Tosylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of a piperidone hydrochloride (1 eq) in dichloromethane was added pyridine (2.1 eq) at 0° C. and the reaction mixture was stirred for 15 min. To this, a solution p-toluene sulfonyl chloride (1.1 eq) in dichloromethane was added at 0° C. and the reaction was continued at room temperature for overnight. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the 1-[(4-methylphenyl)sulfonyl]piperidin-4-one.

Workup

  1. waitthe reaction was continued at room temperature for overnight
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude product, which
  6. customon purification by column chromatography

Sources & evidence

ORD record
ord-5a65fcfc0d4a4ab69d57d2d8390cabbb
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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