Toluene → HCID 13653525, compound

Participants

Reaction Steps

To 250 ml of a 1:1 mixture of toluene:tetrahydrofuran, 35.0 gm N-(n-propyl)-4-t-butylphenoxyacetamide, the product of Example 16, was added. The resulting mixture was heated to reflux and then 42.8 ml borane methylsulfide was added slowly. The reaction mixture was maintained at reflux for 48 hours at which time completion of the reaction was checked by IR spectroscopy. The reaction mixture was then cooled and 200 ml methanol was added slowly to the system. The system was then acidified by bubbling hydrogen chloride gas through it, and then heated to reflux and refluxed for 1 hour. The solvent was removed by stripping; the resulting oil was redissolved in methanol and the methanol stripped. The residue was dissolved in methylene chloride and basified with sodium hydroxide. The methylene chloride solution was then washed with water. The methylene chloride was stripped to give 31.2 gm of the N-(n-propyl)ethanolamine 4-t-butylphenylether.

Provenance & Evidence