Reaction #69597

Reaction equation

1-bromo-1-phenylethane

8-aminoquinoline

1-bromo-1-phenylethane

1-bromo-1-phenylethane

→

title compound

Yield 91.0%

N-(1-Phenylethyl)quinolin-8-amine

Yield 91.0%

Solvents

triethylamine

triethylamine

triethylamine

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting mixture was stirred for additional 2 hr at 120° C
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 2 hr at 120° C
3. 3
   OtherFinally, the product was isolated

Procedure

A mixture of 1.44 g (10.0 mmol) of 8-aminoquinoline, 1.01 g (10.0 mmol) of triethylamine and 1.85 g (10.0 mmol) of 1-bromo-1-phenylethane (1) was stirred for 2 hr at 120° C. One more portion of 1.01 g of triethylamine as well as 1.85 g of 1-bromo-1-phenylethane was added. The resulting mixture was stirred for additional 2 hr at 120° C. One more portion of triethylamine and 1-bromo-1-phenylethane was added, and the reaction mixture was stirred for 2 hr at 120° C. Finally, the product was isolated using flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-ethyl acetate=20:1, vol.) to give 2.26 g (91%) of the title compound.

Source