Dimethylformamide → HCID 70044275, compound

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Reaction Steps

In this example, 4.98 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester was suspended in a mixture solvent of 7.5 ml of dimethylformamide and 30 ml of dichloromethane, and 1.2 ml of thionyl chloride was added thereto under ice cooling. The mixture was stirred under ice cooling for 1.5 hours to make a homogeneous solution. 3.39 g of 1-(1-phenylethyl)-4-hydroxypiperidine was added thereto, and then stirring was effected under ice cooling for 2 hours. After completion of the reaction, the reaction mixture was washed with an aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the concentrated under reduced pressure. The desired product was separated by silica gel column chromatography (eluent:chloroform:methanol=20:1 v/v). The fractions containing the desired product was treated similarly as in Example 2 to obtain 3.44 g of yellow 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-[1-(-phenylethyl)-4-piperidinyl]ester-5-methyl ester hydrochloride (recrystallization solvent: aceton-ethyl acetate) [compound of the general formula (I) wherein R1 =R2 =R4 =CH3, ##STR22## wherein n=0, ##STR23## (yield: 41.2%)

Provenance & Evidence