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

HRID 1019259Notes

Reaction equation

HRID 1019259 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 1 M 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 1 M HCl (100 ml) and brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-40b9d55bd23e4b1c9bbc546d7c8d1cff
Source dataset
uspto-grants-2002_11
Patent number
US06486199B1

Reaction notes

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