Methanesulfonyl chloride → 1-Methyl-2-oxo-3-piperidinyl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([OH:13])[C:8]1=[O:14]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][S:2]([O:13][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH3:6])[C:8]1=[O:14])(=[O:4])=[O:3]Participants
5
Conditions
- Temperature
- 25 °C
Procedure
Methanesulfonyl chloride (0.8 ml., 0.01 mole) was added dropwise to a stirred solution of 1-methyl-2-oxo-3-piperidinol (1.29 g, 0.01 mole) and 4-dimethylaminopyridine (2.44 g., 0.02 mole), in 50 ml. methylene chloride at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 15 min. and at 25° C. for 2.5 hours. The reaction mixture was then washed with 50 ml. saturated aqueous sodium chloride solution containing 6.8 ml. of 6N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate and concentrated in vacuo to a thick oil of the title compound (1.8 g., 87% yield). NMR (CDCl3): 1.6-2.37 (c, 4H); 2.96 (s, 3H); 3.1-3.4 (c) and 3.24 (s) (total 5H); and 4.9 (m, 1H)ppm.
Workup
- customat 0° C.
- washThe reaction mixture was then washed with 50 ml
- additionsaturated aqueous sodium chloride solution containing 6.8 ml
- dry with materialof 6N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate
Sources & evidence
- ORD record
- ord-58db7a1c6e7446e784feaf79cbd0c6ab
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04772597
Reaction notes
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