Hydrochloric Acid → 2-Aminoindan hydrochloride

Participants

Reaction Steps

Amide 25 (0.62 g, 3.0 mmol) was dissolved in 8 mL of dry ether, and BH3 (16 mL of a 1 M solution in THF) was added dropwise, over a 1 h period. After the addition was completed, the reaction mixture was heated to reflux for 1 h. The mixture was cooled to room temperature, and 1.6 mL of water was added cautiously. Subsequently, 3.2 mL of 10% HCl was added, and all volatile solvents were evaporated under reduced pressure. The remaining aqueous solution was basified with 10% NaOH and extracted with ethyl acetate (2 20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure, which yielded 23 as a clear oil (0.52 g, 90%): 1H-NMR (CDCl3, 200 MHz) 0.92 (t, J=7.3, 3H), 1.43-1.61 (m, 2H), 2.58-2.71 (m, 4H), 3.00-3.11 (m, 2H), 3.52-3.65 (m, 3H), 6.49 (d, J=7.8, 1H), 6.55 (s, 1H), 6.96 (d, J=7.8, 1H); 13C NMR 11.6, 23.2, 38.9, 39.9, 50.0, 59.8, 111.5, 113.4, 125.0, 131.6, 142.9, 145.0; MS (EIPI) m/e 190 (M+). Part of the product was converted to the dihydrochloride and recrystallized from ethanol, yielding white crystals: mp 238-242° C. Anal Calcd (Obsd) for C12H18N2.2HCl: C: 54.96 (54.59), H: 7.63 (7.66), N: 10.69 (10.46).

Provenance & Evidence