Thionyl Chloride → HCID 13362116, compound

Participants

Reaction Steps

Thionyl chloride (0.36 ml) is combined with 1-(6-hydroxyhexyl)-3-methyl-2-(3-pyridyl)indole (1.37 g) at 0° . The mixture is then stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate is added and the mixture is extracted with dichloromethane. The extract is washed with brine and dried over anhydrous magnesium sulfate. Concentration in vacuo yields the crude chloride as an oil. Purification by silica gel chromatography (CH2Cl2 /EtOAc 9.5:0.5) gives 1-(6-chlorohexyl)-3-methyl-2-(3-pyridyl)indole as a light yellow oil; NMR (CDCl3) δ3.30 (t, 2H), 3.92 (t, 2H).

Provenance & Evidence