Potassium Hydroxide → N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carboxyethyl)indol-1-yl]acetamide

Participants

Reaction Steps

To a suspension of 0.7 g (1.4 mmol) of N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carbethoxyethyl)indol-1-yl]acetamide in 20 ml of ethanol is added a solution of 0.2 g of potassium hydroxide in 3 ml of water. The mixture is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is dissolved in water and the resulting solution adjusted to pH 4 with 1N aqueous HCl solution. The precipitate which forms is extracted into ethyl acetate. The organic solution is washed with brine, dried over magnesium sulfate and concentrated in vacuo to give N-methyl-N-phenethyl-2-[5-benzyloxy-3-(2-carboxyethyl)indol-1-yl]acetamide as a beige powder (m.p. 122°-125° C.).

Provenance & Evidence