4-Toluenesulfonyl chloride → 1-Tosylpiperidin-4-one

HRID 1071846Notes

Reaction equation

HRID 1071846 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2723901Piperonylamine

Product 1

HCID 5609571-Tosylpiperidin-4-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-piperidone monohydrate hydrochloride (7.68 g, 50 mmol) in methylene chloride (50 ml) were added sequentially p-toluenesulfonyl chloride (10.50 g, 55.07 mmol) and triethylamine (21 ml). The mixture was stirred at room temperature for 16 h before being quenched with water (100 ml). The organic layer was washed with 1M HCl (100 ml) and brine (100 ml), and dried over sodium sulfate. Evaporation of the solvent gave the desired ketone (8.60 g, 68%) as a colorless solid. mp 130-132° C.; 1H NMR (500 MHz, CDCl3) δ2.40 (s, 3H), 2.58 (t, J=6.4 Hz, 4H), 3.38 (t, J=6.4 Hz, 4H), 7.35 (d, J=7.8 Hz, 2H), 7.68 (d, J=8.3 Hz, 2H).

Workup

  1. custombefore being quenched with water (100 ml)
  2. washThe organic layer was washed with 1M HCl (100 ml) and brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b302f5cec5ba4d6294fd055c6f1d7cca
Source dataset
uspto-grants-2005_06
Patent number
US06906205B2

Reaction notes

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