Benzyl Bromide → 1-Benzyl-4-piperidone

A mixture of 4-piperidone monohydrate hydrochloride (2.5 g, 14.56 mmol) and anhydrous potassium carbonate (7 g, 50.64 mmol) in dry DMF (25 mL) was stirred for 30 min at room temperature. Benzyl bromide (2 mL, 16.82 mmol) was added dropwise into the reaction mixture and heated at 65° C. for 14 h. The reaction mixture was cooled to room temperature, filtered and quenched with ice water (25 mL). The resulting mixture was extracted in ethyl acetate (2×20 mL) and the combined organic layers were washed with water (2×15 mL) followed by brine (20 mL). The organic phase obtained was dried over anhydrous sodium sulphate and evaporated. The crude product obtained was purified by crystallisation using 2% methanol in chloroform to afford the title compound.

1. temperatureheated at 65° C. for 14 h
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered
4. customquenched with ice water (25 mL)
5. extractionThe resulting mixture was extracted in ethyl acetate (2×20 mL)
6. washthe combined organic layers were washed with water (2×15 mL)
7. customThe organic phase obtained
8. dry with materialwas dried over anhydrous sodium sulphate
9. customevaporated
10. customThe crude product obtained
11. customwas purified by crystallisation

ORD record

ord-35226734a3a84dbc86eade7739764028

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2