4-[3-(Methylsulfanyl)phenyl]-1-propylpiperidin-4-ol → 4-[3-(Methylsulfanyl)phenyl]-1-propyl-1,2,3,6-tetrahydropyridine

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Reaction Steps

4-(3-Methylsulfanyl-phenyl)-1-propyl-piperidin-4-ol (1) (100 mg, 0.38 mmol) was dissolved in 2 mL of trifluoroacetic acid (TFA) in a 50 mL flask while stirring in a nitrogen atmosphere. The reaction mixture was heated to reflux on an isomantle. After 15 minutes the reaction mixture was cooled to room temperature. The TFA was removed by distillation under reduced pressure. The remaining brown oil was dissolved in diethyl ether, washed 3 times with water and once with brine. The aqueous layers and brine layer were collected, basified with Na2CO3 and extracted with diethyl ether twice. The organic layers were collected, dried on MgSO4, filtered and the solvent was evaporated under reduced pressure using a rotavapor. Yield: 103 mg (111%). GCMS (EI): m/z 247 (M+), 218 (M−29); GC (100-320° C., 15° C./min): 7.6 min.

Provenance & Evidence