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

HRID 2280367Notes

Reaction equation

HRID 2280367 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>FC(F)(F)C(O)=O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 299817804-[3-(Methylsulfanyl)phenyl]-1-propylpiperidin-4-ol

Product 1

HCID 166553434-[3-(Methylsulfanyl)phenyl]-1-propyl-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux on an isomantle
  3. customThe TFA was removed by distillation under reduced pressure
  4. dissolutionThe remaining brown oil was dissolved in diethyl ether
  5. washwashed 3 times with water
  6. customThe aqueous layers and brine layer were collected
  7. extractionextracted with diethyl ether twice
  8. customThe organic layers were collected
  9. customdried on MgSO4
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure
  12. customGC (100-320° C., 15° C./min)
  13. custom7.6 min.

Sources & evidence

ORD record
ord-18dd3df15804462e86125706e3c70c57
Source dataset
uspto-grants-2015_09
Patent number
US09139525B2

Reaction notes

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