Triethylamine → HCID 10156526, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (0.70 g, 2.19 mmol) in methyl sulfoxide (20 mL) was added 5-fluoro-2-(4-piperidinylmethyl)-1H-indole (0.51 g, 2.19 mmol) and triethylamine (0.25 g, 2.30 mmol) and the reaction mixture was heated to 90° C. for 8 h. The reaction mixture was allowed to cool to room temperature and was diluted with dichloromethane (200 mL), washed with water (2×100 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 a colorless oil which was dissolved in ethyl alcohol (5 mL) and treated with a solution of oxalic acid dihydrate (0.244 g, 1.94 mmol) in ethyl alcohol (10 mL). The resulting solid was filtered, washed (hexanes), and dried to give 0.370 g (44%) of 2-{[1-(3,4-dihydro-2H-chromen-2-ylmethyl)-4-piperidinyl]methyl}-5-fluoro-1H-indole as a white solid. mp 187-190° C.; Anal. Calcd. for C24H27FN2O.0.5 C2O4H2.0.5H2O: C, 69.43; H, 6.76; N, 6.48. Found: C, 69.23; H, 6.83; N, 6.48.

Provenance & Evidence