Trifluoroacetic acid → 4-(2-(Methylsulfinyl)phenyl)piperidine

HRID 1108030Notes

Reaction equation

HRID 1108030 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH3:25])=[O:24])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:25][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226222471-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine

Product 1

HCID 187003874-(2-(Methylsulfinyl)phenyl)piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of Step 4 (0.5 g) was treated with trifluoroacetic acid (10 mL) and heated at reflux temperature for 45 minutes. The reaction mixture was cooled, diluted with toluene (40 mL) and evaporated. This procedure was repeated two more times. The residue was treated with CH2Cl2 (70 mL) and adjusted to alkaline pH via addition of NH4OH solution. The organic layer was separated, dried over MgSO4, filtered and evaporated to give 4-(2-methylsulfinylphenyl)piperidine (0.3 g).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 45 minutes
  3. temperatureThe reaction mixture was cooled
  4. customevaporated
  5. additionThe residue was treated with CH2Cl2 (70 mL)
  6. additionvia addition of NH4OH solution
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-5949296e1be34bedbe3dd516b08dde39
Source dataset
uspto-grants-2000_05
Patent number
US06063926

Reaction notes

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