Triethylamine → HCID 9967998, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (0.311 g, 0.98 mmol) in methyl sulfoxide (20 mL) was added 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.500 g, 2.52 mmol) and triethylamine (0.318 g, 3.14 mmol) and the reaction mixture was heated to 80° C. for 3 h. The reaction mixture was allowed to cool to room temperature and was diluted with ethyl acetate (200 mL), washed with water (3×100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, methanol:dichloromethane 1:19) provided 0.180 g (58%) of 3-[1-(3,4-dihydro-2H-chromen-2-ylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole as a pale yellow solid. mp 171-173° C.; Anal. Calcd. for C23H24N2O: C, 80.20; H, 7.02; N, 8.13. Found: C, 79.97; H, 7.02; N, 8.14.

Provenance & Evidence