Sodium Iodide → (R)-2-Hydroxymethyl-1-[3-(4-methoxyphenyl)propyl]piperidine
Reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.S(O[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
(R)-2-hydroxymethylpiperidine (288 mg, 2.50 mmol), 3-(4-methoxyphenyl)propyl mesylate (915 mg, 3.75 mmol), sodium carbonate (398 mg, 3.75 mmol) and sodium iodide (30 mg, 0.20 mmol) were added to acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 hours. The solvent was evaporated under reduced pressure. The residue was distributed in ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water and dried over magnesium sulfate. Then the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane as the eluent and then with dichloromethane and methanol (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-2-hydroxymethyl-1-[3-(4-methoxy-phenyl) propyl]piperidine in the form of a light yellow oil (422 mg, 64%).
Workup
- temperaturewere heated
- customThe solvent was evaporated under reduced pressure
- washThe organic layer was washed with water
- dry with materialdried over magnesium sulfate
- customThen the solvent was evaporated under reduced pressure
- washThe product was eluted with dichloromethane as the eluent
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-405fd2795f4448eab5b165fef8003740
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528504B2
Reaction notes
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