Water → ethyl 1-(dimethylcarbamoyl)piperidine-4-carboxylate

Ethyl isonipecotate (31.44 g, 200 mmol) and triethylamine (50.2 ml, 360 mmol) were dissolved in dichloromethane (200 ml), and under ice cooling, to the solution was added dropwise N,N-dimethylcarbamoyl chloride (27.6 ml, 300 mmol). The mixture was stirred for 18 hours while the temperature was elevating to room temperature. To the reaction mixture was added water (100 ml) under ice cooling, and the organic layer was taken by separatory funnel. The aqueous layer was extracted with dichloromethane (50 ml×2) and the extracts were mixed with the organic layer. The combined organic layer was washed with 1N-hydrochloric acid (100 ml×3), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound (51.30 g, It was proved that N,N-dimethyl carbamoyl chloride is contained about 10 wt % by 1H NMR.) as a pale brown oily substance.

1. customwas elevating to room temperature
2. customthe organic layer was taken by separatory funnel
3. extractionThe aqueous layer was extracted with dichloromethane (50 ml×2)
4. additionthe extracts were mixed with the organic layer
5. washThe combined organic layer was washed with 1N-hydrochloric acid (100 ml×3)
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-42f4b64f2e874f98bc9c6a3c00094047

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348324B2