Dimethylcarbamoyl Chloride → HCID 66718480, compound

Temperature

40 °C

To a stirred solution of 2-(4-hydroxytetrahydropyran-4-yl)pyridine-N-oxide (3.69 g, 18.91 mmol) in anhydrous dichloromethane was added dimethylcarbamoyl chloride (3.05 g, 28.4 mmol) and trimethylsilylcyanide (2.82 g, 28.4 mmol). The mixture was stirred for sixty hours at 40° C., after which time further aliquots of dimethyl carbamoyl chloride (3.05 g, 28.4 mmol) and trimethylsilylcyanide (2.82 g, 28.4 mmol) were added. After stirring at 40° C. for a further 24 hours, sodium carbonate solution (50 mL, 2 M aqueous solution) was added and the mixture stirred overnight. The resultant mixture was filtered and the layers partitioned. Sodium carbonate solution (50 mL, 2 M aqueous solution) was again added to the organic phase and stirred overnight. After separation of the phases, the organic layer was blown down at ambient temperature to give the title compound as a brown oil which was used in the next step without further purification; LC-MS Retention time 1.62 min, (M+H)+ 205.

1. stirringAfter stirring at 40° C. for a further 24 hours
2. stirringthe mixture stirred overnight
3. filtrationThe resultant mixture was filtered
4. customthe layers partitioned
5. additionSodium carbonate solution (50 mL, 2 M aqueous solution) was again added to the organic phase
6. stirringstirred overnight
7. customAfter separation of the phases
8. customwas blown down at ambient temperature

ORD record

ord-657bdcf5574f4d09884858cf3be04ccc

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450328B2