Potassium Iodide → (3S,5S)-1-(3-hydroxypropyl)-3,5-dimethylpiperidine

HRID 657617Notes

Reaction equation

HRID 657617 reaction equation
Cl.[CH3:2][C@H:3]1[CH2:8][C@H:7]([CH3:9])[CH2:6][NH:5][CH2:4]1.Cl[CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[OH:14][CH2:13][CH2:12][CH2:11][N:5]1[CH2:6][C@@H:7]([CH3:9])[CH2:8][C@H:3]([CH3:2])[CH2:4]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 68909796trans-3,5-Dimethylpiperidine;hydrochloride

Product 1

HCID 26722617(3S,5S)-1-(3-hydroxypropyl)-3,5-dimethylpiperidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (3S,5S)-3,5-dimethylpiperidine, hydrochloride (2.58 g), 3-chloropropanol (1.44 mL), potassium carbonate (3.58 g) and a catalytic amount of potassium iodide in acetone (10 mL) is stirred under reflux for 24 h. Precipitate is filtrated and rinsed with acetone. Filtrate is concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol/triethylamine from 80/20/1 to 50/50/1 to give 1.9 g of (3S,5S)-1-(3-hydroxypropyl)-3,5-dimethylpiperidine as a yellow oil.

Workup

  1. temperatureunder reflux for 24 h
  2. filtrationPrecipitate is filtrated
  3. washrinsed with acetone
  4. concentrationFiltrate is concentrated under reduced pressure
  5. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol/triethylamine from 80/20/1 to 50/50/1

Sources & evidence

ORD record
ord-ef7057412092429c8e57998cdc4d7eee
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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