반응 #2320105

반응 방정식

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

1-iodo-propane

→

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

반응 조건

후처리

1. 1
   기타Then 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
   기타to reach r.t.
5. 5
   workup.ADDITIONTo the mixture was added 10% Na2CO3 solution (20 ml)
6. 6
   추출The aqueous layer was extracted with CH2Cl2
7. 7
   건조the combined organic phases were dried (MgSO4)
8. 8
   여과filtered
9. 9
   기타evaporated to dryness
10. 10
    기타The crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v))
11. 11
    기타Collection of the fractions
12. 12
    workup.ADDITIONcontaining pure
13. 13
    기타product and evaporation of the solvent

실험 절차

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)

출처