Editing Synthesis of oleylamine (section)

==== Lab scale purification<br> ====

To a 250 cm3 round-bottomed flask fitted with magnetic stirrer, nitrogen inlet, temperature probe, condenser and a 100 cm3 pressure-equalized dropping funnel, was charged crude elaidylamine (17.0 g, 63.6 mmol) and '''t-butyl methyl ether''' (85 cm3, 5 volumes). The substrate did not dissolve, so an additional 85 cm3 of TBME was added. Although a solution was not obtained, the resultant slurry was deemed adequate for further processing. The stirred slurry was treated with 37% '''hydrochloric acid''' (7.6 g, 1.2 eq.). During this addition the slurry became very thick and difficult to stir, suggesting that '''elaidylamine hydrochloride is poorly soluble in TBME'''. '''Water (100 cm3) was therefore added''' which eventually yielded a clear monophasic solution. The hydrochloride was then precipitated by addition to excess '''acetonitrile''' (750 cm3). The resultant suspension was cooled to 0-5°C, stirred for 30 minutes, filtered and washed with cold acetonitrile (2 x 200 cm3). The solid was then dried under vacuum at 30-35°C to yield elaidylamine hydrochloride as a white crystalline powder (12.1 g, 63%) The hydrochloride (12.1 g) was then slurried in TBME (180 cm3, 15 volumes) and treated with 2M sodium hydroxide solution (40 cm3, 2 eq.). During the addition the solid dissolved to give a bi-phasic solution which was stirred overnight. The mixture was then transferred to a separating funnel, the'''lower aqueous layer removed,''' and the organic phase washed with water (2 x 50 cm3). The resultant product solution was then evaporated to yield elaidylamine as clear oil, which solidified upon cooling to room temperature (10.7 g, 100% from hydrochloride, 63% from crude amine).<br>

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[[Category:Transfection]] [[Category:Paul]]