2-(4-methoxy-3-phenylmethoxyphenyl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 45 parts of benzoyl chloride in 149 parts of chloroform is added portionwise over a 30 minute period to a solution of 78 parts of 3-benzyloxy-4-methoxyphenethylamine in 72 parts of triethylamine and 596 parts of chloroform. The mixture is stirred at room temperature for an additional 90 minutes. It is then washed twice with water and once with dilute aqueous sodium bicarbonate solution, dried over anhydrous calcium sulfate and stripped to a low volume under reduced pressure. Addition of n-hexane results in crystallization of N-(3-benzyloxy-4-methoxyphenethyl)benzamide. That product melts at about 136°-138°C. It is then washed twice with water and once with dilute aqueous sodium bicarbonate solution dried over anhydrous calcium sulfate Addition of n-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 20 parts of lithium aluminum hydride in 444 parts of tetrahydrofuran and 177 parts of ethyl ether is added portionwise, over a 1 hour period, a warm solution of 56 parts of 3-benzyloxy-4-methoxy-β-nitrostyrene in 267 parts of tetrahydrofuran. The reaction mixture is refluxed for an additional 2 hours, then is cooled in ice and decomposed by adding 40 parts of water in 71 parts of tetrahydrofuran, followed by 40 parts by volume of a 25% by weight aqueous sodium hydroxide solution, followed by 40 parts of water. The salts are removed by filtration and the filtrate is dried over anhydrous calcium sulfate and stripped of solvent under reduced pressure to afford, as an oil, 3-benzyloxy-4-methoxyphenethylamine. is added portionwise, over a 1 hour period The reaction mixture is refluxed for an additional 2 hours is cooled in ice The salts are removed by filtration the filtrate is dried over anhydrous calcium sulfate