Acetone → HCID 131714202, compound

Participants

Reaction Steps

4-(2-Chlorophenyl)-2-[(1-benzyl-2-imidazolyl)methoxymethyl]-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (Example 10) (2 g) was dissolved in ethanol (70 ml) and acidified with hydrogen chloride gas. Then 10% palladium on charcoal catalyst (0.25 g) was added and the suspension was stirred under hydrogen at 50 p.s.i and room temperature overnight. Examination of the reaction mixture by t.l.c. showed that about one third of the starting material had been converted to a more polar product. The catalyst was removed by filtration, the ethanol was evaporated and the residue partitioned between chloroform (50 ml) and dilute aqueous ammonia (30 ml). The chloroform solution was dried (Na2CO3), filtered and evaporated. The residue was dissolved in a little toluene and chromatographed on silica (t.l.c. grade, 6 g). Elution with toluene removed unreacted starting material; elution with chloroform and then chloroform plus 2-4% v/v methanol gave the product, which was converted to the hydrochloride salt by addition of ethereal hydrogen chloride to an acetone solution of the free base. Recrystallisation of the hydrochloride salt from methanol-ethyl acetate (1:4) gave the title compound (430 mg), m.p. 190° C.

Provenance & Evidence