Reaction #56613

Reaction equation

Methyl-4-oxo-4-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]butanoate

allylamine

ammonium chloride

→

N-Allyl-4-oxo-4-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]butanamide

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureunder reflux for 6 h
3. 3
   Extractionextracted with ethyl acetate
4. 4
   DryingThe combined organic phases are dried (Na2SO4)
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude product (17.7 g, content: 84.5%, HPLC, 100% method) is recrystallized from toluene

Procedure

Methyl-4-oxo-4-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]butanoate (VIII-a-1) (18.2 g, 52 mmol) is treated with allylamine (41.6 g, 730 mmol) and ammonium chloride (1.8 g, 33 mmol) and heated under reflux for 6 h. For work-up, the mixture is poured into ice-cold aqueous HCl (2 M) and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4) and concentrated. The crude product (17.7 g, content: 84.5%, HPLC, 100% method) is recrystallized from toluene.

Source