Hydrochloric Acid → HCID 19068310, compound

Participants

Reaction Steps

In a 100-ml round-bottomed flask were placed n-laurylamine (11.1 g (60 mmol)) and isovaniline (1.52 g (10 mmol)) under nitrogen. While stirring, diisopropylether (17.5 ml) and glacial acetic acid (5 ml) were sequentially added dropwise. After completion of addition, the mixture was stirred for approximately 2 hours at room temperature, followed by the addition of a borane-pyridine complex (1.2 ml (10 mmol), product of Aldrich) over 10 minutes. The mixture was stirred for a further 2 hours. Subsequently, 5N-HCl (12 ml) was added dropwise and the resultant mixture was stirred for 10 minutes. The pH of the mixture was turned to basic using an aqueous 5N--NaOH solution. The product formed was extracted using diisopropyl ether, concentrated, and purified via silica gel column chromatography n-hexane:ethyl acetate=2:1), thereby obtaining 2.6 g of N-lauryl-3-hydroxy-4-methoxybenzylamine as mud yellow crystals (yield: 82%).

Provenance & Evidence