Acetic Acid → 2-Propylamino-5-methoxytetralin

Participants

Reaction Steps

This compound was prepared following Procedure A from 5-methoxy 2-tetralone (6.0 g, 34.0 mmol), acetic acid (5.1 ml, 102 mmol), propyl amine (5.5 ml, 68 mmol), and NaCNBH3 (5.3 g, 85 mmol) to give 4.63 g of 32b (62%, free base). 1H NMR (free base) (400 MHz, CDCl3) 0.92-0.964 (t, 3H, J=7.6 Hz), 1.39 (bs, 1H), 1.49-1.61 (m, 3H), 2.05-2.10 (m, 1H), 2.53-2.62 (m, 2H), 2.66-2.70 (t, 3H, J=7.6 Hz), 2.87-2.94 (m, 2H), 2.98-3.03 (m, 1H), 3.81 (s, 3H), 6.65-6.67 (d, 1H, J=8 Hz), 6.96-6.71 (d, 1H, J=8 Hz), 7.07-7.11 (t, 1H, J=7.2 Hz).

Provenance & Evidence