1-Bromopentane → Benzamide, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(pentyloxy)-, hydrochloride (1:1)

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Reaction Steps

A mixture of 5-(2-tert-butylamino-1-hydroxyethyl) salicylamide, hydrochloride (8.7 g) and anhydrous potassium carbonate (8.25 g) in dimethylformamide (100 ml) were heated at 100° for 1 hour. 1-Bromopentane (4.5 g) in dimethylformamide (25 ml) was added and the mixture was heated at 100° for a further 2 hours. The solvent was removed and the residue was partitioned between water and ethyl acetate. The dried (MgSO4) ethyl acetate solution was evaporated to yield a red oil which was chromatographed on alumina. Eluation with ethyl acetate gave the required benzamide which was obtained as a colourless oil which was converted into its hydrochloride (1.55 g) m.p. 162°-167°. Recrystallisation from ethyl acetate-methanol raised the m.p. to 169°-172°.

Provenance & Evidence