Hydrochloric Acid → N-(4-(4-(Ethylheptylamino)butyl)phenyl)methanesulfonamide

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Reaction Steps

A stirred solution of N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide as prepared in Preparation 3 (2.0 g, 0.005 mol) in THF (20 ml), under N2, is treated during 1 hour with a 1M solution of borane dimethylsulfide in CH2Cl2 (15.8 ml, 0.0158 mol). The mixture is kept at ambient temperature for 30 minutes and at reflux for 4 hours. It is then cooled in an ice bath and treated slowly with MeOH (2 ml). This mixture is kept at ambient temperature for 18 hours, acidified with a solution of HCl in EtOH and refluxed for 1 hour. The cooled solution is concentrated and the residue is mixed with saturated NaHCO3 and extracted with CH2Cl2. The extracts are washed with brine, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (350 g) with 5% MeOH-0.5% NH4OH--CH2Cl2. The N-[4-[4 -(ethylheptylamino)butyl]phenyl]methanesulfonamide thus obtained is mixed with saturated NaHCO3 and extracted with Et2O. The extracts are washed with brine, dried (MgSO4) and concentrated. A solution of the residue in pentane is filtered through Magnisol and concentrated. MS: theory for C20H36N2O2S(M+): 368.2497. Found: 368.2498.

Provenance & Evidence