Sodium Hydroxide → HCID 54766095, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-Amino-3-[3-(2-(dimethylamino)ethyl)-1-(4-phenoxyphenyl)-1H-indol-5-yl]propan-1-ol (48) was prepared as follows: A mixture of compound 45 prepared in Example 11 (0.2 g, 0.4 mmol), 4 mL NaOH (2N aqueous) and 4 mL of ethanol was shaken at 80° C. for 2 hours. After cooling to room temperature, the reaction mixture was extracted with CHCl3, concentrated and purified by column (silica gel, EtOAc/MeOH/NH4OH 80/20/2) to give compound 48 as a sticky oil, which was dissolved in 10 mL of HCl (0.2N aqueous), and freeze dried to afford a white solid (110 mg, HCl-salt, ˜50%): 1H-NMR (400 MHz, CD3OD) δ: 7.72 (s, 1H), 7.49-7.54 (m, 4H), 7.4-7.44 (m, 2H), 7.16-7.22 (m, 4H), 7.07-7.11 (m, 2), 3.73-3.75 (m, 1H), 3.53-3.62 (m, 4H), 3.08-3.12 (m, 2H), 3.1 (s, 6H); LC/MS: m/z=430.1 [M+H]+ (Calc: 429.5).

Provenance & Evidence