Thiophenol → 2-(1,1-dioxido-4-thiomorpholinyl)-N-(2-methoxyethyl)ethanamine

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-N-(2-methoxyethyl)-2-nitrobenzenesulfonamide (0.470 g, 1.12 mmol) and thiophenol (0.369 g, 3.35 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.616 g, 4.46 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave the title compound as a yellow solid (0.222 g, 84% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 237 (M+H+), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 2.15 (br. s., 1H) 2.66-2.71 (m, 2H) 2.71-2.77 (m, 2H) 2.82 (t, J=5.04 Hz, 2H) 2.97-3.05 (m, 4H) 3.05-3.10 (m, 4H) 3.37 (s, 3H) 3.51 (t, J=5.04 Hz, 2H).

1. filtrationfiltered
2. customto remove unwanted solids
3. concentrationThe crude filtrate was concentrated in vacuo
4. dissolutionredissolved in methanol
5. washUndesired materials were eluted from the cartridge with methanol
6. washthe desired material was released from the resin by elution with 2M ammonia in methanol
7. concentrationConcentration in vacuo

ORD record

ord-387d61c3f6eb4e2b8725475003d0a8d9

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846647B2