2-(4-methoxy-1H-indol-3-yl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. evaporate in vacuo to remove the MeOH leaving a thick orange oil Dissolve the oil in MeOH add dropwise to Et2O (200 mL) giving a gummy white precipitate Stir with heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine LiAlH4 (6.78 g; 178.74 mmol; 6 eq) and anhydrous THF. Dissolve 3-(2-nitrovinyl)-4-methoxy-1H-indole (6.5 g; 29.79 mmol) in anhydrous THF and add dropwise to the LiAlH4 solution with vigorous stirring. After the addition is complete, heat to reflux. After 1 hour cool to ambient temperature and stir. After 16 hours, quench the excess LiAlH4 as described in J. Med. Chem. 1995, 38, 2050. Filter the gray suspension through celite and rinse the celite with ethyl acetate. Evaporate the filtrate in vacuo to residue. Chromatograph the residue on silica gel eluting with 1 L of CHCl3MeOH/NH4OH (95:10:1) and then 1 L of CHCl3/MeOH/NH4OH (90:10:1) as the mobile phase. Pool fractions containing the product and evaporate to give the title compound as a tan solid: 1H NMR (300 MHz, d6-DMSO): 2.96 (t, 2H); 3.42 (t, 2H); 3.83 (s, 3H); 6.42 (dd, 1H); 6.93 (m, 3H); 10.7 (s, 1H); MS (ES+): m/z 191 (M+H)+; 174 (M−NH2)+; 159 (M−OCH3)+; (ES−): m/z 189 (M−H)−. After the addition heat to reflux quench the excess LiAlH4 Filter the gray suspension through celite rinse the celite with ethyl acetate Evaporate the filtrate in vacuo to residue Pool fractions containing the product evaporate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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, 4 H); 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. evaporate in vacuo to remove the MeOH leaving a thick orange oil Dissolve the oil in MeOH add dropwise to Et2O (200 mL) giving a gummy white precipitate Stir with heating