Sodium Hydroxide → 3-(2-Chloroethoxy)-N-(2-pyridylmethyl)propanamide

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A cooled solution of (2-pyridyl)methanamine (0.55 g, 5.1 mmol) in CH2Cl2 was stirred vigorously with 2% aqueous NaOH (12.2 mL, 6.1 mmol) while 3-(2-chloroethoxy)propanoyl chloride (6.1 mmol, prepared by refluxing 3-(2-chloroethoxy)propanoic acid with SOCl2) in CH2Cl2 was added dropwise. The same NaOH solution was then used to maintain pH at 9, and at costant pH the layers were separated. The organic phase was washed with 3 N HCl, with H2O, and then dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/AcOEt, 1:1, as eluent) to afford pure compound in 65% yield. 1H NMR (CDCl3): δ 2.38-2.41 (m, 2H), 2.60-2.63 (m, 2H), 3.54-3.60 (m, 2H), 3.66-3.69 (m, 2H), 4.45 (d, 2H, J=6.1 Hz), 6.12 (br t, 1H, D2O exchanged), 7.09-7.11 (m, 2H), 8.40-8.42 (m, 2H).

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