Tetrahydrofuran → HCID 21474842, compound

Participants

Reaction Steps

Borane-dimethylsulfide complex (10-10.2M, 35 ml, 1.2 eq) was added to a refluxing solution of N-[2-(2,6-dimethylphenoxy)-1-methylethyl]-acetamide (68 g, 0.289 mol) and tetrahydrofuran (400 ml) under a nitrogen atmosphere. After the addition was complete, the reaction was allowed to reflux for 25 hours. The reaction was then cooled to room temperature and 10% hydrochloric acid/ethanol was added until the mixture was acidic. After concentration of the reaction mixture, ethyl ether was added to induce crystallization. The solids were isolated by filtration and dried to give [2-(2,6-dimethylphenoxy)-1-methylethyl]-ethylamine hydrochloride salt (53.0 g, 75% yield, mp 184.7-185.8° C.).

Provenance & Evidence