Cyclohexylamine → N-Cyclohexyl-4-methoxy-3-piperazin-1-ylbenzenesulfonamide hydrochloride

A solution of cyclohexylamine (91 mg) in dichloromethane (1 ml) was added slowly to a stirred solution of 3-(4-trichloroacetylpiperazin-1-yl)-4-methoxybenzenesulfonyl chloride (D2) (200 mg) in dichloromethane (2 ml). The mixture was stirred overnight then washed with 1M HCl (4 ml) and water (4 ml), dried and concentrated to a solid. The solid was dissolved in tetrahydrofuran or 1,4-dioxane (5 ml) and to the solution was added 0.15M potassium hydroxide solution (5 ml) and the whole stirred at ambient temperature for 8 hours. The solution was concentrated to remove the organic solvent and the aqueous residue was extracted with dichloromethane (2×20 ml). The combined extracts were dried, acidified with 1M ethereal hydrogen chloride (1 ml), concentrated to an oil and stirred with acetone/diethyl ether to afford the title compound (E1) (28 mg, 21%). δH (250 MHz, d6-DMSO) 1.10 (5H, br, s), 1.56 (5H, br, s), 2.86 (1H, br, s), 3.21 (8H, br, s), 3.87 (3H, s), 7.13 (1H, d, J=8.0 Hz), 7.33 (1H, s), 7.46-7.52 (2H, m), 9.19 (2H, br, s), MH+354.

1. washthen washed with 1M HCl (4 ml) and water (4 ml)
2. customdried
3. concentrationconcentrated to a solid
4. dissolutionThe solid was dissolved in tetrahydrofuran
5. addition1,4-dioxane (5 ml) and to the solution was added 0.15M potassium hydroxide solution (5 ml)
6. stirringthe whole stirred at ambient temperature for 8 hours
7. concentrationThe solution was concentrated
8. customto remove the organic solvent
9. extractionthe aqueous residue was extracted with dichloromethane (2×20 ml)
10. customThe combined extracts were dried
11. concentrationconcentrated to an oil
12. stirringstirred with acetone/diethyl ether

ORD record

ord-a6163165f5f94d1d9de67e428c766637

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548504B1