Thionyl Chloride → 3-(1-Chloroethyl)-5,6,7,8-tetrahydroisoquinoline

Temperature

0 °C

3-(1-Hydroxyethyl)-5,6,7,8-tetrahydroisoquinoline (360 mg, 2.0 mmole) was dissolved in 4 ml dichloromethane in a 25 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated dropwise with thionyl chloride (218 μl, 3.0 mmole) in 3 ml dichloromethane, and is stirred 2 h at 0° C. followed by 1.5 h at room temperature. The mixture is recooled to 0° C., is quenched with 20 ml saturated sodium bicarbonate, and the layers are separated. The aqueous layer is extracted with 4×10 ml dichloromethane and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to an amber oil. The crude material is chromatographed over 30 g silica gel (230-400 mesh), eluting with 20% acetone/hexane, while collecting 5 ml fractions. Fractions 11-16 are combined and concentrated to afford 339 mg (87%) of 3-(1-chloroethyl)-5,6,7,8-tetrahydroisoquinoline.

1. waitfollowed by 1.5 h at room temperature
2. customis recooled to 0° C.
3. customis quenched with 20 ml saturated sodium bicarbonate
4. customthe layers are separated
5. extractionThe aqueous layer is extracted with 4×10 ml dichloromethane
6. dry with materialthe combined organics are dried over potassium carbonate
7. concentrationThe dried organics are concentrated in vacuo to an amber oil
8. customThe crude material is chromatographed over 30 g silica gel (230-400 mesh)
9. washeluting with 20% acetone/hexane
10. customwhile collecting 5 ml fractions
11. concentrationconcentrated

ORD record

ord-42ec37babbdd4905b4e56bdcc7ccdfaf

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043248