Reaction #2186198

Reaction equation

1,2,3,4-Tetrahydro-quinolin-7-ol

1-bromo-2-fluoroethane

diisopropylethylamine

→

desired product

Yield 44.0%

1-(2-Fluoro-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ol

Yield 44.0%

Solvents

DMF

Conditions

Workup

1. 1
   ExtractionThe reaction mixture is extracted with 0.1 N aqu
2. 2
   WashThe combined organic extracts are washed with brine
3. 3
   Dryingdried over sodium acetate
4. 4
   Otherevaporated
5. 5
   Otherchromatographed (silica gel, ethyl acetate/petroleum ether 1:2 to 1:1)

Procedure

500 mg (3.35 mmol) 1,2,3,4-Tetrahydro-quinolin-7-ol are dissolved in 8 mL DMF and stirred at 60° C. overnight with 0.325 mL (1.3 eq) 1-bromo-2-fluoroethane, in the presence of 0.63 mL (1.1 eq) diisopropylethylamine. The reaction mixture is extracted with 0.1 N aqu. HCl and ethyl acetate. The combined organic extracts are washed with brine, dried over sodium acetate and evaporated. The residue is column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2 to 1:1) to yield 290 mg (44%) desired product as a brown oil.

Source