Acetone → HCID 53998669, compound

Participants

Reaction Steps

A solution of 3.0 g (0.014 mole) of N-[3-(2-aminoethyl)-1H-indol-5-yl]urea, Example 1, in 100 ml MeOH was treated with 1.11 ml of acetone followed by 1.32 g (0.021 mole) of NaBH3CN and stirred for 18 hours. The solvent was removed in vacuo and the residue carefully dissolved in 20 ml of 20% HCl, heated for 15 minutes, cooled and neutralized with 4N NaOH to pH=12. The precipitated oil was extracted into EtOAc, dried over MgSO4, filtered and evaporated to give a glassy white solid. This material was purified by column chromatography (0.75% NH4OH/MeOH on silica gel) followed by recrystallization from acetone to give desired product: m.p. 145.5°-147°.

Provenance & Evidence