تفاعل #2320105

معادلة التفاعل

4-Pyridin-4-yl-2-trifluoromethyl-phenylamine

1-iodo-propane

→

4-(1-Propyl-1,2,3,6-tetrahydro-pyridine-4-yl)-2-trifluoromethyl-phenylamine

ظروف التفاعل

المعالجة

1. 1
   أخرىThen the voilatiles were evaporated
2. 2
   workup.DISSOLUTIONthe residue redissolved in abs EtOH (20 ml)
3. 3
   workup.ADDITIONNaBH4 (800 mg) was added portions wise at −20° C
4. 4
   أخرىto reach r.t.
5. 5
   workup.ADDITIONTo the mixture was added 10% Na2CO3 solution (20 ml)
6. 6
   استخلاصThe aqueous layer was extracted with CH2Cl2
7. 7
   تجفيفthe combined organic phases were dried (MgSO4)
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated to dryness
10. 10
    أخرىThe crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v))
11. 11
    أخرىCollection of the fractions
12. 12
    workup.ADDITIONcontaining pure
13. 13
    أخرىproduct and evaporation of the solvent

الإجراء التجريبي

4-Pyridin-4-yl-2-trifluoromethyl-phenylamine (270 mg) was dissolved in 1-iodo-propane (2 ml) and heated to 100° C. for 2 h. Then the voilatiles were evaporated and the residue redissolved in abs EtOH (20 ml) and NaBH4 (800 mg) was added portions wise at −20° C. The mixture was then allowed to reach r.t. and stirred over night. To the mixture was added 10% Na2CO3 solution (20 ml). The aqueous layer was extracted with CH2Cl2 and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v)). Collection of the fractions containing pure product and evaporation of the solvent afforded pure 4-(1-Propyl-1,2,3,6-tetrahydro-pyridine-4-yl)-2-trifluoromethyl-phenylamine (200 mg). MS m/z (rel. intensity, 70 eV)) 284 (M+, 53), 255 (bp), 144 (40), 127 (39), 70 (39). Rf 0.28 (MeOH)

المصدر