Hydrochloric Acid → 2-Aminoindan hydrochloride

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).

1. additionAfter the addition
2. temperaturethe reaction mixture was heated
3. temperatureto reflux for 1 h
4. customall volatile solvents were evaporated under reduced pressure
5. extractionextracted with ethyl acetate (2 20 mL)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated under reduced pressure, which

ORD record

ord-439579a1329d4a6dbe7c3f07bc7ed3bd

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291494B1