Hydrochloric Acid → HCID 11793231, compound

Participants

Reaction Steps

Sodium hydride (63.5% oil dispersion, 0.66 g) is added to a solution of thiocresol (2.2 g) in toluene (40 ml) under ice-cooling and the mixture is stirred at room temperature for 30 minutes. A solution of 1-(3,4,5-trimethoxybenzyloxymethyl)-1-(2-thienyl)-N,N-dimethylpropylamine (2.2 g) in toluene (20 ml) is added to the mixture under ice-cooling and hexamethylphosphoric triamide (3 ml) is added thereto. The mixture is refluxed in nitrogen atmosphere for 5 hours. After cooling, 10% hydrochloric acid is added to the mixture and the aqueous layer is collected therefrom. The aqueous layer is washed with ether and adjusted to pH 8 with sodium bicarbonate and then extracted with ether. The extract is dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=100:1). The resulting product is recrystallized from a mixture of ethyl acetate and n-hexane, whereby 1-(4-hydroxy-3,5- dimethoxybenzyloxymethyl)-1-(2-thienyl)-N,N-dimethylpropylamine (2 g) is obtained as colorless pillars.

Provenance & Evidence