Reaktion #578051

Reaktionsgleichung

4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxylic acid

thionyl chloride

intermediate ( 15 )

(±)-methyl 1-(4-aminophenyl)-α-phenyl-4-piperidineacetate

DIPEA

→

methyl α-phenyl-1-[4-[[[4′-(trifluoromethyl)-[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetate

Ausbeute 77.3%

Lösungsmittel

DCM

DMF

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for one hour
2. 2
   SonstigeThe solvent was evaporated
3. 3
   workup.ADDITIONDCM (50 ml) was added twice
4. 4
   Sonstigethe solvent was evaporated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in DCM (20 ml)
6. 6
   workup.STIRRINGThe mixture was stirred at room temperature for three hours
7. 7
   Waschenwashed with water
8. 8
   SonstigeThe organic layer was dried
9. 9
   Sonstigethe solvent was evaporated
10. 10
    SonstigeThe residue was crystallized from 2-propanol
11. 11
    FiltrationThe precipitate was filtered off
12. 12
    Sonstigedried

Vorschrift

DMF (0.5 ml) was added to a solution of 4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxylic acid (0.014 mole) in DCM (50 ml) and thionyl chloride (0.028 mole). The mixture was stirred and refluxed for one hour. The solvent was evaporated. DCM (50 ml) was added twice and the solvent was evaporated. The residue was dissolved in DCM (20 ml) and this solution was added to a mixture of intermediate (15) (0.014 mole) and DIPEA (0.028 mole) in DCM (80 ml). The mixture was stirred at room temperature for three hours and washed with water. The organic layer was dried and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and dried, yielding 6.2 g of methyl α-phenyl-1-[4-[[[4′-(trifluoromethyl)-[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-4-piperidineacetate (melting point 151° C.) identified as compound No. 39 in the following table F-1.

Quelle