Phenoxyacetic Acid → 2-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

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A mixture of (-)-2-(N-n-propylamino)-5-methoxytetralin (80 mg, 31.9 mmol; prepared according to J. Chem. Soc., 1965, pp 26-36), phenoxyacetic acid (166 mg, 109.4 mmol) and borane trimethylamine complex (80 mg, 109.4 mmol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSo4, filtered and concentrated. The resulting oil was subjected to flash chromatography (Silica: 9:1 pet ether/EtOAc) and product was isolated with characteristic peaks at: NMR (300 MHz, CDCl3); δ 7.3-6.6 (m, 8H), 4.0(t,2H), 3.7(S,3H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4(m,3H) 0.9(t,3H).

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