Toluene → 2-(Phenoxymethyl)morpholine

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2-Aminoethyl hydrogen sulphate (49 g, 0.347 mol) was added in portions to a mixture of (±)-1,2-epoxy-3-phenoxypropane (11.2 ml, 0.083 mol), sodium hydroxide (26.4 g, 0.66 mol) in water (50 ml) and methanol (20 ml). After addition the reaction mixture was stirred at 40° C. (oil bath temperature) for 2 hours. The reaction mixture was cooled, sodium hydroxide pellets (20.65 g, 0.516 mol) and toluene (80 ml) were added, then the reaction mixture stirred, whilst heating at 65° C. (oil bath temperature) for 7.5 hours. The reaction mixture was cooled, toluene (40 ml) and water (140 ml) were added. The toluene phase was extracted with 2M hydrochloric acid (2×60 ml). The acid extracts were combined, 40% sodium hydroxide solution added to pH=11, then extracted with toluene (2×60 ml). The combined organics were dried (sodium sulphate) then evaporated to give a colourless gum (10 g) which was purified by column chromatography on silica, using neat ethyl acetate to remove the lipophilic impurities then ethyl acetate/methanol/ammonia (9:1:0.1) to elute the required product as a colourless oil (7.0 g, 44%). Rf 0.22 in dichloromethane/methanol (9:1) on silica plates MS CI+, m/z=194 for (M+H)+. 1H NMR (360 MHz, CDCl3) δ2.54-2.85 (2H, m), 2.92 (1H, ddd, J1 =2, J2 =J3 =12 Hz), 3.05 (1H, dd, J1 =2, J2 =12 Hz), 3.67 (1H, ddd, J1 =2, J2 =J3=12 Hz), 3.83-4.03 (4H, m), 6.88-6.97 (3H, m), 7.23-7.30 (2H, m).

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