1-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine → 4-(2-(Methylsulfinyl)phenyl)piperidine

HRID 2256050Notes

Reaction equation

HRID 2256050 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>[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

3

Reactant 1

HCID 226222471-Benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine

Product 1

HCID 187003874-(2-(Methylsulfinyl)phenyl)piperidineYield 83.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(2-methylsulfinylphenyl)piperidine (1.66 g) in 8 mL of trifluoroacetic acid was heated to reflux for 45 minutes. At the end of this period, the reaction mixture was evaporated and the residue was treated with toluene. Upon evaporating the solvent, the residue was treated with an additional portion of toluene and the process was repeated. The final residue was dried under reduced pressure and purified by chromatography; elution with dichloromethane:methanol:triethylamine (19:1:1) afforded the named product (0.87 g); MS: 224; NMR: 1.6-2.4 (m, 4), 2.7 (two peaks, 3), 2.9-3.2 (m, 3), 3.3-3.5 (m, 2), 5.3-5.7 (br, 1), 7.4-7.5 (m, 3), 7.9-8.0 (m, 1).

Workup

  1. temperatureto reflux for 45 minutes
  2. customAt the end of this period, the reaction mixture was evaporated
  3. additionthe residue was treated with toluene
  4. customUpon evaporating the solvent
  5. additionthe residue was treated with an additional portion of toluene
  6. dry with materialThe final residue was dried under reduced pressure
  7. custompurified by chromatography
  8. washelution with dichloromethane:methanol:triethylamine (19:1:1)

Sources & evidence

ORD record
ord-c30efc5ee7bf4ce7b3bcb7f8bee00e91
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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