Potassium Carbonate → 1-(Methylsulphonyl)piperidin-4-one
Reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>CC(C)=O>[CH3:16][S:17]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)(=[O:19])=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a suspension of 4-piperidone monohydrate hydrochloride (2.0 g, 13 mmol) and K2CO3 (9.0 g, 65.2 mmol) in acetone (40 ml) was added methanesulfonyl chloride (5.96 g, 52.1 mmol) at 0-5° C. The mixture was stirred at 25° C. for 24 h. The solid material was removed by filtration, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography (silica gel, 80% ether in hexanes) to afford the desired ketone (1.20 g, 52%) as a colorless solid. mp 102-104° C.; 1H NMR (500 MHz, CDCl3) δ2.58 (t, J=6.4 Hz, 4H), 2.90 (s, 3H), 3.60 (t, J=6.4 Hz, 4H).
Workup
- customThe solid material was removed by filtration
- concentrationthe filtrate was concentrated to dryness
- customThe residue was purified by flash chromatography (silica gel, 80% ether in hexanes)
Sources & evidence
- ORD record
- ord-fe5143b8d331447e9b038b47eb339972
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486199B1
Reaction notes
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