Benzyl Chloride → (1-Benzyl-4-piperidyl)methanamine

HRID 2110034Notes

Reaction equation

HRID 2110034 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4][CH2:5]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 235274-(Aminomethyl)piperidine

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving 4-aminomethylpiperidine (5.754 ml, 50 mmol) in acetonitrile (200 ml), potassium carbonate (13.82 g, 100 mmol) and benzyl chloride (17.13 g, 150 mmol) were added and the mixture was stirred at 60° C. overnight. Upon completion of the reaction, the reaction mixture was filtered and the solvent was distilled off. A developing solvent (CH2Cl2/MeOH/NEt3 90/5/5) was used for purification by silica gel column chromatography to obtain (1-benzyl-4-piperidyl)methylamine. The compound was identified by LC-MS.

Workup

  1. additionwere added
  2. customUpon completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. distillationthe solvent was distilled off
  5. customA developing solvent (CH2Cl2/MeOH/NEt3 90/5/5) was used for purification by silica gel column chromatography

Sources & evidence

ORD record
ord-e244ad9cd20b4dfa8d63b6bbd021852f
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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