Hydrochloric Acid → 2-[(Methylsulfonyl)methyl]piperidine

HRID 1063960Notes

Reaction equation

HRID 1063960 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=[O:4])=[O:3].Cl>C(O)C.O=[Pt]=O>[CH3:1][S:2]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14958256HCID 14958256, compound

Product 1

HCID 222752132-[(Methylsulfonyl)methyl]piperidineYield 90.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

2-(Methylsulfonylmethyl)pyridine (4.40 g, 0.0257 moles) and PtO2 (0.50 g) were suspended in ethanol (80 mL) with 1N HCl (15 mL). The mixture was hydrogenated at 50 psi for 18 hours. The catalyst was filtered and the solvent removed. The residue was dissolved in CH2Cl2 and washed with sat. Na2CO3. The aqueous layer was extracted with CH2Cl2 (3×25 mL). The organic layers were combined and dried over Na2SO4 and evaporated to give a yellow oil (4.11 g, 90%) which solidified on standing. Further purification was unnecessary. LCMS (178, M+H).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent removed
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with sat. Na2CO3
  5. extractionThe aqueous layer was extracted with CH2Cl2 (3×25 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-13eb0f30e9ec42dd90368c66d1a9a5ac
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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