Sodium Hydroxide → (6-Bromo-indan-2-yl)-dipropyl-amine

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydride (90 mg, 2.36 mmol) and aluminium chloride (350 mg, 2.25 mmol) were added to dry THF (25 mL). The mixture was cooled to -15° C. and kept at this temperature for 15 min. N-(6-Bromo-indan-2-yl)-N-propyl-propionamide (preparation 14, 0.35 g, 1.13 mmol) dissolved in dry THF (10 mL) was added and the reaction mixture was stirred at -15° C. for 90 min. Aqueous NaOH (15 mL, 15%) was added and the mixture extracted with ethyl acetate. The layers were separated and the organic layer washed with water, dried (Na2CO3) and the solvent was evaporated to dryness. The crude product was chromatographed and the pure fractions were pooled, yielding 280 mg (83%) of (6-bromo-indan-2-yl)-dipropyl-amine as the free base. The amine was converted to its hydrochloride salt with EtOH-HCl and recrystallized from a mixture of 2-propanol and isopropyl ether. m.p. 196°-198° C. (HCl); 1H NMR (300 MHz, CDCl3) δ 0.90 (t, 6H), 1.50 (m, 4H), 2.50 (t, 4H), 2.75-3.08 (m, 4H), 3.60-3.75 (p, 1H), 7.05 (d, J=8 Hz, 1H), 7.28 (d, J=8 Hz, 1H), 7.32 (s, 1H); 13C NMR (75.4 MHz, CDCl3) δ 12.02, 20.30, 36.25, 36.62, 53.39, 63.25, 119.82, 125.95, 127.56, 129.26, 141.00, 144.47; MS m/e 295 (6, M+), 269 (100), 266 (98), 116 (54), 115 (41).

Provenance & Evidence