Hydrochloric Acid → 2-[(Methylsulfonyl)methyl]piperidine
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst was filtered
- customthe solvent removed
- dissolutionThe residue was dissolved in CH2Cl2
- washwashed with sat. Na2CO3
- extractionThe aqueous layer was extracted with CH2Cl2 (3×25 mL)
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-13eb0f30e9ec42dd90368c66d1a9a5ac
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06967196B1
Reaction notes
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