Methyl p-toluenesulfonate → 1,1-Dimethyl-3-hydroxypiperidinium p-toluenesulfonate

HRID 344782

Reaction equation

HRID 344782 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3]1.[C:9]1([CH3:20])[CH:14]=[CH:13][C:12]([S:15]([O:18]C)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CC(C)=O>[C:9]1([CH3:20])[CH:10]=[CH:11][C:12]([S:15]([O-:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1.[CH3:1][N+:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3]1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 980163-Piperidinol, 1-methyl-

Product 1

HCID 150522081,1-Dimethyl-3-hydroxypiperidinium p-toluenesulfonateYield 164.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 20 ml of acetone was dissolved 2.30 g of 1-methyl-3-piperidinol, and 3.72 g of methyl p-toluenesulfonate was added dropwise to the resulting solution. The mixture was stirred at room temperature, heated under reflux, and cooled to precipitate crystals. The crystals were collected by filtration and dried to give 4.94 g of the desired product, m.p. 125°-127° C. (decomp.).

Workup

  1. additionwas added dropwise to the resulting solution
  2. temperatureheated
  3. temperatureunder reflux
  4. temperaturecooled
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-250ba9a0ebc94da1951455139c8420cc
Source dataset
uspto-grants-1991_10
Patent number
US05053402

Linked notes

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