Reaction #2320105

Reaction equation

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

1-iodo-propane

→

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

Conditions

Workup

1. 1
   OtherThen 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
   Otherto reach r.t.
5. 5
   workup.ADDITIONTo the mixture was added 10% Na2CO3 solution (20 ml)
6. 6
   ExtractionThe aqueous layer was extracted with CH2Cl2
7. 7
   Dryingthe combined organic phases were dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated to dryness
10. 10
    OtherThe crude product was purified by flash chromatography (MeOH: CH2Cl2 (1:9 (v/v))
11. 11
    OtherCollection of the fractions
12. 12
    workup.ADDITIONcontaining pure
13. 13
    Otherproduct and evaporation of the solvent

Procedure

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)

Source