Sodium hydride → HCID 59375077, compound

A solution of 3-bromo-2-methylaniline (1 g, 5.37 mmol) in DCM (15 mL) was treated with TEA (0.749 mL, 5.37 mmol) and then dropwise with a solution of 5-bromopentanoyl chloride (1.072 g, 5.37 mmol) in DCM (4 mL). The mixture was stirred at rt for 30 min, then was diluted with DCM, washed with water and brine, and dried and concentrated. The residue was dissolved in THF (100 mL) and added to a suspension of sodium hydride (60% oil dispersion, pre-washed with hexane, 0.430 g, 10.75 mmol) in THF (50 mL). The resulting mixture was stirred overnight at rt. The mixture was concentrated and the residue was acidified with 1 M hydrochloric acid. The mixture was extracted with DCM and the organic phase was washed with water, dried and concentrated to give 1-(3-bromo-2-methylphenyl)piperidin-2-one as a tan oil (1.4 g, 97%). 1H NMR (400 MHz, chloroform-d) δ 7.49-7.54 (1 H, m), 7.07-7.13 (2 H, m), 3.38-3.60 (2 H, m), 2.54-2.59 (2 H, m), 2.26 (3 H, s), 1.91-2.02 (4H, m). Mass spectrum m/z 268, 270 (M+H)+.

1. washwashed with water and brine
2. customdried
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in THF (100 mL)
5. stirringThe resulting mixture was stirred overnight at rt
6. concentrationThe mixture was concentrated
7. extractionThe mixture was extracted with DCM
8. washthe organic phase was washed with water
9. customdried
10. concentrationconcentrated

ORD record

ord-6f48a49161394d999f5baa9c03127386

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362065B2