反应详情

A stirred solution of N-[4-[2-(ethylheptylamino)ethyl]phenyl]methanesulfonamide as prepared in Example 3 (0.332 g, 0.975 mmol) in acetonitrile (3 ml) is treated with HOAc, (0.056 ml, 0.975 mmol) and ethyl bromide (0.73 ml, 9.75 mmol). The solution is refluxed for 1 day, treated with additional ethyl bromide (1 ml) and acetonitrile (3 ml) and refluxed for one additional day. The mixture is concentrated; the residue is mixed with a solution of NaHCO3 (160 mg) in water and extracted with Et2O. The extracts are washed with water, dried (MgSO4) and concentrated to give recovered starting material (0.15 g, identified by TLC). The aqueous layers are combined, made strongly basic with 1N KOH, saturated with potassium bromide and washed with CH2Cl2. The aqueous layer is then acidified with 48% hydrogen bromide and extracted with CH2Cl2. The extracts are washed with saturated potassium bromide, dried (NaSO4) and concentrated to give 0.15 g of N,N-diethyl-N-heptyl-4-[(methylsulfonyl)amino]benzeneethanaminium bromide. MS calc'd for C20H37N2O2S (M+): 369.2576. Found: 369.2585.

1. temperatureThe solution is refluxed for 1 day
2. temperaturerefluxed for one additional day
3. concentrationThe mixture is concentrated
4. additionthe residue is mixed with a solution of NaHCO3 (160 mg) in water
5. extractionextracted with Et2O
6. washThe extracts are washed with water
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto give
10. customrecovered
11. washwashed with CH2Cl2
12. extractionextracted with CH2Cl2
13. washThe extracts are washed with saturated potassium bromide
14. dry with materialdried (NaSO4)
15. concentrationconcentrated