Thionyl Chloride → 1-(1-Chloroethyl)-5,6,7,8-tetrahydroisoquinoline

Participants

Reaction Conditions

Reaction Steps

1-(1-Hydroxyethyl)-5,6,7,8-tetrahydroisoquinoline (1.77 g, 10 mmole) is dissolved in 30 ml dichloromethane in a 100 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated dropwise with thionyl chloride (1.1 ml, 15 mmole) in 5 ml dichloromethane, and is stirred 2 h at 0° C. followed by 1 h at room temperature. The mixture is recooled to 0° C., is quenched with 50 ml saturated sodium bicarbonate, and the layers are separated. The aqueous layer is extracted with 3×25 ml dichloromethane and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to a yellow oil. The crude material is chromatographed over 50 g silica gel (230-400 mesh), eluting with 10% acetone/hexane, while collecting 9 ml fractions. Fractions 10-24 are combined and concentrated to afford 1.96 g (100%) of 1-(1-chloroethyl)-5,6,7,8-tetrahydroisoquinoline.

Provenance & Evidence