Reaction #1528399

Reaction equation

2-(4-fluoro-phenyl)-1-phenyl-ethylamine

2-chloroethyl isocyanate

→

title compound

Yield 65.6%

(4,5-Dihydro-oxazol-2-yl)-[2-(4-fluoro-phenyl)-1-phenyl-ethyl]-amine

Yield 65.6%

Solvents

THF

Conditions

Workup

1. 1
   Otherwas evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in dimethoxy ethane (25 ml)
3. 3
   workup.ADDITIONDBU (1,8-diazabicyclo[5.4.0]undec-7-en) was added (1.78 g)
4. 4
   Temperaturethe reaction mixture heated
5. 5
   Temperatureunder reflux for 1 hour

Procedure

A solution of 2-(4-fluoro-phenyl)-1-phenyl-ethylamine (1.50 g) in THF was treated dropwise with 2-chloroethyl isocyanate (0.89 g) at 0° C. After stirring overnight at room temperature the solvent was evaporated and the residue dissolved in dimethoxy ethane (25 ml). DBU (1,8-diazabicyclo[5.4.0]undec-7-en) was added (1.78 g) and the reaction mixture heated under reflux for 1 hour. Column chromatography on silica yielded 1.3 g of the title compound.

Source