Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

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Reaction Steps

1-(4-Nitrophenoxy)-2,3-epoxypropane (Reference Example 19, 4.3 g) was dissolved in methanol (30 ml) and DMF (10 ml). Dimethylamine (2M solution in methanol, 17 ml) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness and the residue was dissolved in saturated sodium bicarbonate solution and EtOAc. The EtOAc layer was separated and washed twice with saturated brine, dried over anhydrous sodium sulphate, filtered and evaporated to give the title product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3, 300 MHz): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3 H), 7.00 (d, 2H), 8.20 (d, 2H); m/z: (ES+) 241 (MH+).

Provenance & Evidence