Sodium Iodide → (1-(Pyridin-4-ylmethyl)piperidin-3-yl)methanol

HRID 1598370Notes

Reaction equation

HRID 1598370 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.Cl[CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>C(C(C)=O)C>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 18933428(1-(Pyridin-4-ylmethyl)piperidin-3-yl)methanolYield 93.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3-hydroxymethylpiperidine (5.0 g, 43 mmol) in methyl ethyl ketone (50 ml) were added successively potassium carbonate (60 g, 0.43 mol), sodium iodide (1.30 g, 8.68 mmol), 4-chloromethylpyridine hydrochloride (8.54 g, 52.1 mmol) and the mixture was heated under reflux for 8 hours. The reaction mixture was filtered with Celite and the solvent was distilled off from the filtrate under reduced pressure. The residue was chromatographed using silica gel column and the fraction from methanol-chloroform (1/20) gave 3-hydroxymethyl-1-(4-pyridylmethyl)piperidine (8.29 g). Yield=93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. filtrationThe reaction mixture was filtered with Celite
  4. distillationthe solvent was distilled off from the filtrate under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-68db796509ed4c44a3e50e3ae2074965
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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