Pyridine → HCID 19775329, compound

Participants

Reaction Steps

Methanesulphonyl chloride (40 μl) was added dropwise to a stirred solution of 2-[N-(4-aminomethylbenzyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane (140 mg -- see Example 46) in pyridine (5 ml) and the mixture was stirred at room temperature or 16 hours and evaporated. The residue was azeotroped twice with toluene, dissolved in 2M hydrochloric acid, washed with ether, basified with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (3 g) using methylene chloride plus 0-5% methanol as the eluant. Appropriate fractions were combined and evaporated and the residue was dissolved in ether and treated with excess saturated ethereal hydrogen chloride. The resulting precipitated gum was collected and triturated with ether to give the title compound as a colourless solid which was characterised as a hemihydrate (31 mg, 17%), m.p. 150°-155°.

Provenance & Evidence