Schiff base condensation with bulky amine

SyntheticPage 719
Published Feb 27, 2014


Reaction Scheme

Procedure

An oven dried  50 ml round bottom  two necked flask, equipped with a spin bar, a septa, a water condenser and a Nitrogen inlet at the top,  was charged  with 12.5 mL of anhydrous ethanol and 1.03 g (9.6 mmole) of freshly distilled piconilaldehyde. After mixing, 2.0 mL (10.6 mmole) of 2,6-diisopropylaniline were added through the septa with the aid of an hypodermic syringe and  the reaction mixture was brought to reflux using a heating mantle.  Reflux was kept for an hour and then the system was let to cool down to room temperature. Solvent and reagent excess were removed by means of a rotatory evaporator to give a yellow solid in quantitative yield.  The product is sufficiently pure for most purposes but it may be recrystallized from n-pentane at -25oC to give yellow crystals with yields oscillating from  80-85%. 

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