Hydrochloric Acid → HCID 20550950, compound

Participants

Reaction Steps

An ice-cold solution of 5-[2-[(1-methyl-3-phenylpropyl)imino]-1-oxopropyl]thiophene-3-carboxamide (0.7 g) in methanol (50 ml) was treated portionwise with sodium borohydride (0.76 g), stirred at 0° for 1 h, poured onto ice, acidified with dilute hydrochloric acid (2 N), neutralised with aqueous sodium bicarbonate (8%), and extracted with ethyl acetate (2×300 ml). The extract was washed with brine (50 ml) and evaporated to a small volume (ca. 20 ml) to deposit a fine white solid (0.47 g) which was partitioned between ethyl acetate (2×300 ml) and aqueous sodium bicarbonate (1 M; 100 ml). The organic solution (MgSO4) was dried and evaporated to give an off-white foam which was dissolved in ethyl acetate (ca. 100 ml) and treated with ethereal hydrogen chloride to precipitate the title compound (0.42 g) m.p. 125°-130°. TLC SiO2 (3% Et3N/20% i-PrOH/EtOAc) Rf 0.22 and 0.27.

Provenance & Evidence