Acetic Acid → 2-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

Participants

Reaction Steps

To a solution of indole-7-carboxaldehyde (10.0 g, 68.9 mmol) in 1,2-dichloroethane (300 mL) stirred under N2 at 20–24° C. was added ethanolamine (8.5 mL, 140.8 mmol), acetic acid (4.0 mL, 70.0 mmol) and NaBH(OAc)3 (16.8 g, 75.3 mmol). The resulting mixture was stirred at 20–24° C. overnight. The mixture was diluted with CH2Cl2 (200 mL), washed carefully with NaHCO3 (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×200 mL). The combined organic layer was washed with brine (100 mL) and dried over Na2SO4, filtered and concentrated in vacuo to give 12.4 g (95%) of the crude amine as a light yellow solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 10.93 (s, 1 H), 7.41–7.39 (d, 1 H, J=7.81 Hz), 7.29 (s, 1 H), 7.0–6.99 (d, 1 H, J=6.84 Hz), 6.93–6.89 (t, 1 H, J=8.06 Hz), 6.41–6.4 (d, 1 H, J=2.44 Hz), 4.55–4.45 (bs, 1 H), 3.98 (s, 2 H), 3.49–3.47 (bt, 2 H, J=5.13 Hz), 2.61–2.58 (t, 2 H, J=5.86 Hz).

Provenance & Evidence