2-Bromobutane → 5,6,7,8-Tetrahydro-8-(1-methylpropyl)quinoline

Temperature

-78 °C

A solution of BuLi (6.8 ml, 1.6 M in hexane) was added dropwise to a cold (−78° C.) solution of 5,6,7,8-tetrahydroquinoline (1.33 g, 10 mmol) in THF (20 ml). The mixture was stirred for 10 min at −78° C. and sec-butyl bromide (1.51 g, 11 mmol) was added dropwise. The mixture was allowed to warm up to room temperature during 1 h, was then carefully quenched with water and extracted with MTBE (3×50 ml). The combined organic phases were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The brown residue was distilled bulb-to-bulb to yield 1.69 g (89%) of the title compound as a colorless oil. This is a general synthetic procedure and the other compounds exemplified were made according to this procedure, duly modified to employ the appropriate alkyl halide alkylating agent in order to add the correct alkyl group at the 8-position.

1. temperatureto warm up to room temperature during 1 h
2. customwas then carefully quenched with water
3. extractionextracted with MTBE (3×50 ml)
4. washThe combined organic phases were washed with water and brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. distillationThe brown residue was distilled bulb-to-bulb

ORD record

ord-a0b3314685944649bf1aac193aa7c92d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933231B2