تفاعل #578051

معادلة التفاعل

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

المردود 77.3%

المذيبات

DCM

DMF

DCM

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for one hour
2. 2
   أخرىThe solvent was evaporated
3. 3
   workup.ADDITIONDCM (50 ml) was added twice
4. 4
   أخرىthe 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
   غسيلwashed with water
8. 8
   أخرىThe organic layer was dried
9. 9
   أخرىthe solvent was evaporated
10. 10
    أخرىThe residue was crystallized from 2-propanol
11. 11
    ترشيحThe precipitate was filtered off
12. 12
    أخرىdried

الإجراء التجريبي

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.

المصدر