Water → 4-(4-Chlorophenyl)butan-1-amine

Participants

Reaction Steps

(Ali, F. E.; Dandridge, P. A.; Gleason, J. G.; Krell, R. D.; Kruse, C. H.; Lavanchy, P. G; Snader, K. M. J. Med Chem., 1982, 25, 947). To a stirred suspension of lithium aluminum hydride (2.40 g, 63.2 mmol) in 65 mL diethyl ether was added slowly a solution of (3.12 g 15.8 mmol) of 36a in 28 mL THF, and stirred at rt for 1 h. To the reaction mixture was slowly added 4 mL water, 4 mL 5 N NaOH(aq), and 12 mL water. The organics were removed from the emulsion which was dissolved in water and extracted with ether. The organic portions were dried over Na2SO4(s), and condensed to give 37a (2.76 g, 95%) as an oil. UV λmax 224 (7600, 95% ETHANOL). 1H NMR (400 MHz, CDCl3) δ 7.23 (m, 2H), 7.10 (d, J=8 Hz, 2H), 2.74 (t, J=7 Hz, 2H), 2.60 (t, J=8 Hz, 2H), 2.25 (s, 2H), 1.64 (m, 2H), 1.49 (m, 2H). 13C NMR (CDCl3) δ 141.2, 131.8, 130.1, 128.8, 42.3, 35.4, 33.6, 29.0; IR (liq.) 3365 (b), 3296 (b), 3026, 2933 (s), 2858 (s), 2170 (w), 1996 (w), 1576, 1492 (s), 1460, 1093 (s), 1016 (s), 831, 821, 804, cm−1; HRMS (FAB) calcd for C10H14ClN+H1 184.0893, found 184.0879.

Provenance & Evidence