Hydrogen Bromide → 1-Benzyl-3-(bromomethyl)piperidine

HRID 1681990Notes

Reaction equation

HRID 1681990 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[BrH:22]>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][Br:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 260Hydrogen Bromide2×HCID 11430Potassium CarbonateHCID 10398044(1-Benzylpiperidin-3-yl)methanol

Product 1

HCID 190759011-Benzyl-3-(bromomethyl)piperidine

Procedure

55.1 g (0.268 mol) of N-benzyl-3-(hydroxymethyl)-piperidine are added to 400 ml of 48% hydrobromic acid with vigorous stirring and the mixture is refluxed for 1 hour. Then hydrogen bromide is introduced to saturation point (about 1 hour), the mixture is refluxed for another hour and left to stand overnight. It is then neutralized with solid potassium carbonate whilst cooling with ice and then extracted with methylene chloride. The organic phase is dried over magnesium sulphate and concentrated by evaporation in vacuo. Yield: 52.0 g (72.2% of theory), Rf value: 0.85 (aluminium oxide neutral, eluant: methylene chloride).

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperaturethe mixture is refluxed for another hour
  3. waitleft
  4. temperaturecooling with ice
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-febbf752e8ce4fce902c337609427ffc
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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