反应 #2320105

反应方程式

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

1-iodo-propane

→

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

反应条件

后处理

1. 1
   其他Then 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
   其他to reach r.t.
5. 5
   workup.ADDITIONTo the mixture was added 10% Na2CO3 solution (20 ml)
6. 6
   萃取The aqueous layer was extracted with CH2Cl2
7. 7
   干燥the combined organic phases were dried (MgSO4)
8. 8
   过滤filtered
9. 9
   其他evaporated to dryness
10. 10
    其他The crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v))
11. 11
    其他Collection of the fractions
12. 12
    workup.ADDITIONcontaining pure
13. 13
    其他product and evaporation of the solvent

实验过程

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)

来源