Acetic Acid → N,N-diethyl-N-heptyl-4-[(methylsulfonyl)amino]benzeneethanaminium bromide

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Reaction Steps

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.

Provenance & Evidence