Methanol → HCID 19873366, compound

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Reaction Steps

A stirred solution of N-[4-[2-(ethylheptylamino)-1-hydroxyethyl]phenyl]methanesulfonamide of Example 5 (1.5 g, 0.0042 mol) in acetonitrile (15 ml) is treated with ethyl bromide (6.12 ml, 0.082 mol) and refluxed under N2 for 4 days. Additional ethyl bromide is added and reflux is continued for 3 days. The reaction is still incomplete by TLC on silica gel with 5% MeOH-1% NH4OH--CH2Cl2. The mixture is concentrated and mixed with a solution of NaHCO3 (200 mg) in water and Et2O. The aqueous layer is extracted with Et2O and the Et2O extracts are washed with water. The combined water solution is made alkaline with 1N potassium hydroxide, saturated with potassium bromide and extracted with CH2Cl2. The CH2Cl2 extracts are washed with saturated potassium bromide. The combined aqueous layer is acidified with hydrogen bromide and extracted with CH2Cl2. These extracts are washed with saturated potassium bromide, dried (Na2SO4) and concentrated. This material is pure by HPLC on an RP-18 Spheri-10 column using a gradient of 50% H2O to 35% H2O--CH3CN with both solvents containing 0.2% TFA to yield N,N-diethyl-N-heptyl-β-hydroxy-4-[(methylsulfonyl)amino]benzeneethanaminium bromide.

Provenance & Evidence