1H-Indole-3-ethanamine, 4-methoxy- → 2-(4-methoxy-1H-indol-3-yl)ethan-1-amine hydrochloride

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Reaction Steps

Dissolve 4-methoxytryptamine (1 g, 5.26 mmol) in MeOH and add of NH4Cl (0.97 eq, 0.27 g, 5.10 mmol). After 30 minutes, evaporate in vacuo to remove the MeOH leaving a thick orange oil. Dissolve the oil in MeOH and add dropwise to Et2O (200 mL) with vigorous stirring giving a gummy white precipitate. Stir with heating to give the title compound as a solid: 1H NMR (d6-DMSO, 300 MHz): 3.06 (bs, 4H); 3.86 (s, 3H); 6.46 (dd, 1H); 7.06-6.9 (m, 3H); 7.93 (bs, 1H); 10.9 (s, 1H); MS (ES+): m/z 191 (M+H)+; 175 (M−CH3)+; 174 (M−NH2)+; (ES−): 189 (M−H)−; Analysis for C11H15ClN2O: Calcd.: C, 58.2788; H, 6.6692; N, 12.3566. found C, 58.18; H, 6.73; N, 12.15.

Provenance & Evidence