Chloroacetyl chloride → tert-butyl 4-((2-chloro-N-ethylacetamido)methyl)-4-hydroxypiperidine-1-carboxylate

Temperature

0 °C

To a 100 mL round bottom flask containing tert-butyl 4-((ethylamino)methyl)-4-hydroxypiperidine-1-carboxylate (2.4 g) was added dichloromethane (30 mL) and triethylamine (3 mL, 21.52 mmol). An addition funnel was attached to the flask. The vessel was placed under nitrogen and the solution was cooled to 0° C. with an ice bath. In a separate vial, chloroacetyl chloride (1 mL, 12.48 mmol) was diluted with dichloromethane (20 mL) and transferred to the addition funnel. This mixture was added dropwise to the cold starting material over 10 min. The reaction mixture was then allowed to stir under nitrogen for 3 h while slowly allowing the ice bath to warm to room temperature. The reaction mixture was diluted with dichloromethane (100 mL) and was washed with water (2×50 mL) and brine (1×50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound (3.23 g) which was carried forward without further purification. MS(ES)+ m/e 335.2 [M+H]+.

1. customAn addition funnel was attached to the flask
2. additionThis mixture was added dropwise to the
3. customover 10 min
4. temperatureto warm to room temperature
5. washwas washed with water (2×50 mL) and brine (1×50 mL)
6. customThe organic layer was separated
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-50aeaf4de3c84dce8f9718aea12323a7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09084794B2