N-Methylaniline → 6-[Methyl(phenyl)amino]hexan-1-OL

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Reaction Steps

N-(6-hydroxyhexyl)-N-methylaniline 2 was prepared by mixing N-methylaniline (153 g, 1.43 mol.), 6-chlorohexanol (200 g, 1.46 mol.), potassium carbonate (200 g, 1.45 mol.) and potassium iodide (6 g, catalyst) in 750 mL of n-butanol. The mixture was heated to reflux under argon with vigorous external stirring for 96 hours. The solution was cooled, filtered, and the solvent was removed in vacuo. The residue was distilled under high vacuum to yield 2 (235 g, 79.5% yield) as a colorless oil, having a boiling point of 120°-125° C. (0.05 mm Hg).

Provenance & Evidence