Piperidine → 2-Methyl-5-(2-piperidin-1-yl-ethyl)-1H-indole-3-carboxylic Acid Benzyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (450 mg, 1.16 mmol, Example 56, Step D) in dioxane (10 mL) was added piperidine (1.1 mL, 11.6 mmol). The mixture was stirred at 80° C. for 2 hours and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was recrystallized from ethyl acetate and diethyl ether to give 275 mg (63%) of the desired product as a white solid: mp 159-161° C.; MS(APCI+): m/z 377.1 (MH+); Anal. Calcd for C24H28N2O2.1.04H2O: C, 72.93; H, 7.67; N, 7.09. Found: C, 72.54; H, 7.31; N, 7.04.

Provenance & Evidence