1,2-Dibromoethane → HCID 54593788, compound

Temperature

-78 °C

To a suspension of magnesium (0.426 g, 17.51 mmol) in THF (50 mL) was added 1,2-dibromoethane (0.058 mL, 0.674 mmol) and stirred for 10 min and then 4-chloro-1-methylpiperidine (1.8 g, 13.47 mmol) in THF (4 mL) was added and the mixture was refluxed under nitrogen overnight. Cooled solution of the (1-methylpiperidin-4-yl)magnesium chloride was canulated into a cold (−78° C.) solution of sulfuryl chloride (1.3 mL, 16 mmol) in THF (10 mL). The mixture was stirred at 0° C. for 1.5 h and cooled to −78° C. and bubbled ammonia gas for 10 min and stirred at −78° C. for 10 min and allowed to warm to r.t. maintained under balloon pressure of NH3 for 2 h. Diluted with 100 mL ether, filtered off the solids and the filtrate was concentrated to afford a brown solid. Brown solid in THF was stirred with K2CO3 for 1h and filtered and concentrated to afford 1-methylpiperidine-4-sulfonamide as a beige solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.59 (2 H, m), 1.84 (2 H, m), 1.93 (2 H, m), 2.15 (3 H, s), 2.71 (1 H, ddd, J=12.13, 8.32, 3.66 Hz), 2.84 (2 H, m), 6.69 (2 H, brs).

1. temperaturethe mixture was refluxed under nitrogen overnight
2. stirringThe mixture was stirred at 0° C. for 1.5 h
3. custombubbled ammonia gas for 10 min
4. stirringstirred at −78° C. for 10 min
5. temperatureto warm to r.t.
6. temperaturemaintained under balloon pressure of NH3 for 2 h
7. additionDiluted with 100 mL ether
8. filtrationfiltered off the solids
9. concentrationthe filtrate was concentrated
10. customto afford a brown solid
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-9c7e1f5ba7c945d0829de3bd7571ef6e

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538102B2