Hydrochloric Acid → HCID 70228308, compound

Participants

Reaction Steps

1-[2-[[2-(3-Methoxyphenyl)-2-(2-methylphenyl)ethenyl]oxy]ethyl]-1,2,5,6-tetrahydro-3-pyridine carboxylic acid methyl ester (1.15 g, 0.0027 mol) (prepared as described in Method D) was dissolved in ethanol (15 ml) and 12N sodium hydroxide solution (0.5 ml) was introduced. After stirring the solution at room temperature for 4 h, ice (30 g) was added, and the pH of the reaction mixture was adjusted to ca. 7 with 37% hydrochloric acid solution. Dichloromethane (200 ml) was added, and the pH was further adjusted to ca. 1 with 37% hydrochloric acid solution. Water was added until the solid material was dissolved, and the dichloromethane phase was dried (Na2SO4) and evaporated to an oil, which was co-evaporated three times with acetone. The residue was triturated with diethyl ether to give the title compound (0.60 g, 52%), which gave HPLC retention times of 17.1 and 17.6 min. for the geometric isomers (gradient elution, water/20-80% acetonitrile, both containing 0.1% TFA).

Provenance & Evidence