Acetic Acid → 3-((2(RS)-(Phenoxymethyl)morpholin-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridine Hydrogen Oxalate

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38% Aqueous formaldehyde (0.9 ml) was added dropwise to a stirred solution of 2(RS)-(phenoxymethyl)morpholine (2.10 g, 0.0109 mmol) in glacial acetic acid (8 ml) and water (4 ml). After stirring for 10 minutes this solution was treated with 1H-pyrrolo[2,3-b]pyridine (1.18 g, 0.010 mmol). The reaction mixture was stirred at room temperature for 20 hours. The mixture was poured onto 2M sodium hydroxide solution (180 ml) and extracted with ethyl acetate (3×80 ml). The combined extracts were washed with saturated sodium chloride solution (80 ml), dried (sodium sulphate) then evaporated to give a gum which was purified by column chromatography on silica (300 g) using ethyl acetate/methanol (20:1) to afford the title compound free base (2.30 g, 65%) as a gum. The hydrogen oxalate salt had mp 188°-189° C. (ethanol) MS, CI+, m/z=324 for (M+H)+. 1H NMR (360 MHz, DMSO-d6) δ2.55-2.75 (2H, m), 3.14 and 3.30 (each 2H, each 2H, each d, J=12 Hz), 3.86-4.03 (4H, m), 4.08-4.20 (3H, m), 6.84-7.27 (6H, m), 7.46 (1H, s), 8.07 (1H, dd, J1 =1, J2 =8 Hz), 8.27 (1H, dd, J1 =1, J2 =5 Hz), 11.43 (1H, s). Found: C, 60.61; H, 5.43; N, 9.97. C19H21N3O2.C2H2O4 requires C, 61.01; H, 5.61; N, 10.16%.

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