Sodium Iodide → HCID 69898564, compound

HRID 1859436Notes

Reaction equation

HRID 1859436 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.S(C1C=CC(C)=CC=1)(O[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:3]2[CH2:2][OH:1])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2447732-(4-chlorophenyl)ethyl 4-methylbenzenesulfonateHCID 6950192(2R)-piperidin-2-ylmethanol

Product 1

HCID 69898564HCID 69898564, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

(R)-2-hydroxymethylpiperidine (288 mg, 2.50 mmol), 4-chlorophenethyl tosylate (931 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 and then with dichloromethane and methanol (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-1-(4-chlorophenethyl)-2-hydroxymethylpiperidine in the form of a light yellow oil (354 mg, 56%).

Workup

  1. temperaturewere heated
  2. customThe solvent was evaporated under reduced pressure
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThen the solvent was evaporated under reduced pressure
  6. washThe product was eluted with dichloromethane
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6cbfa1f27a464c5ebcebea80ee8a88ed
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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