Sodium Iodide → (R)-2-hydroxymethyl-1-(3,4-methylenedioxyphenethyl)piperidine

HRID 1859432Notes

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][C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=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][C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(R)-2-hydroxymethylpiperidine (288 mg, 2.50 mmol), 3,4-methylenedioxyphenethyl mesylate (732 mg, 3.00 mmol), sodium carbonate (320 mg, 3.00 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 10 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-methylenedioxyphenethyl)piperidine in the form of a light yellow oil (370 mg, 56%).

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-5405b206a7ba476992d92483f66c146c
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528504B2

Reaction notes

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