Methylamine → HCID 67625240, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-hydroxypropyl)-2-[2-(thiophen-3-yl)vinyl]indole (121 mg) in 3 ml of methylene chloride was treated with 120 μl of 2,6-lutidine and cooled to 0° C. Trifluoromethanesulfonic anhydride (100 μl) was added, and after stirring for 30 minutes 5 ml of 40% aqueous methylamine was introduced, and the reaction mixture stirred at 25° C. for 3 hours. After stirring for a further 12 hours at 0° C., the reaction mixture was partitioned between methylene chloride and water, the organic layer dried, and solvent was removed under reduced pressure. Preparative TLC on silica gel (eluting with 10% methanol/methylene chloride) gave 83 mg of 1-[3-(methylamino)propyl)-2-[2-(thiophen-3-yl)vinyl]indole (67%). This product was dissolved in 3 ml of methylene chloride containing 150 μl of pyridine and trifluoracetic anhydride (40 μl) was added. After 30 minutes, the mixture was partitioned between diethylether and aqueous sodium bicarbonate, the organic layer dried, and solvent was removed under reduced pressure. Preparative TLC on silica gel (eluting with 3:1 hexane/EtOAc) gave 80 mg of 1-[3-(N-methyltrifluoromethylacetamido)propyl)-2-[2-(thiophen-3-yl)vinyl]indole (73%).

Provenance & Evidence