Hydrochloric Acid → HCID 68902946, compound

Participants

Reaction Steps

In an analogous manner to EXAMPLE 1, step 3 (2SR,3RS)-4-(2-hydroxy-3-indol-1-yl-3-phenyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester was prepared from (2RS,3RS)-toluene-4-sulfonic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester (EXAMPLE 1, step 3, 0.211 g, 0.5 mmol) and tert-butyl-1-piperazine carboxylate (0.19 g, 1.0 mmol). The product was dissolved in diethyl ether (3 mL) and treated with a 4N solution of hydrochloric acid in dioxane (0.75 mL, 3.0 mmol). The reaction mixture was then stirred at room temperature for 15 hours, and the crude solid product was filtered and recrystallized from ethanol with a minimum amount of diethyl ether to give the titled compound, (1RS,2SR)-1-(1H-indol-1-yl)-1-phenyl-3-piperazin-1-ylpropan-2-ol dihydrochloride as a tan solid. MS (ESI) m/z 336 ([M+H]+); HRMS: calcd for C21H25N30+H+, 336.20704; found (ESI, [M+H]+), 336.2085.

Provenance & Evidence