Hydrochloric Acid → N-propyl-2,3-dihydro-1H-inden-2-amine

Participants

Reaction Steps

2-Propionamidoindan (24, 0.83 g, 4.4 mmol) was converted to 28 (0.75 g, 98%), as described for the reduction of 25. A small amount was converted to the hydrochloride and recrystallized from 2-propanol, which yielded white crystals: mp 191-192° C.; 1H-NMR (CDCl3, 200 MHz) 1.04 (t, J=7.3, 3H), 1.70-1.82 (m, 2H), 3.01-3.20 (m, 4H), 3.29-3.48 (m, 2H), 4.00-4.11 (m, 1H), 7.18-7.30 (m, 4H); 13C NMR 9.7, 19.3, 35.5 (2C), 47.6, 58.0, 124.2 (2C), 127.0 (2C), 138.6 (2C). HRMS calcd. (obsd.) for C12H17N 175.1361 (175.1364).

Provenance & Evidence