Sodium Hydroxide → HCID 53973983, compound

Participants

Reaction Steps

(R)-N-(2-(3-(3-Methylphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (3.5 g, 8.6 mmol) was dissolved in 96% ethanol (10 ml) and a 12 N sodium hydroxide solution (2.2 ml) was added. The reaction mixture was stirred at room temperature for 4 h. The solvent was evaporated in vacuo and dichloromethane (100 ml) and water (10 ml) were added. A concentrated hydrochloric acid solution (3.4 ml) was added with cooling on an ice-bath. The phases were separated and from the organic phase the solvent was evaporated in vacuo. Water (100 ml) was added to the residue and the aqueous solution was washed with small portions of ethyl acetate. The aqueous phase was reduced to approx. 10 ml in vacuo. Dichloromethane (250 ml) and water (40 ml) were added and pH of the solution was adjusted to 8.5 with a 4 N sodium hydroxide solution. The phases were separated and the organic phase was dried (Na2SO4). The solvent was evaporated in vacuo to give 2.4 g (74%) of the title compound.

Provenance & Evidence