3,4-Dichlorobenzyl chloride → HCID 43130924, compound

HRID 2109985Notes

Reaction equation

HRID 2109985 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:13][N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH2:1])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 235274-(Aminomethyl)piperidine

Product 1

HCID 43130924HCID 43130924, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving 4-aminomethyl-piperidine (10 g) in acetonitrile (250 ml), 3,4-dichlorobenzyl chloride (5.8 g) and potassium carbonate (5 g) were added at room temperature, and the mixture was stirred at 60° C. overnight. The reaction mixture was filtered, the solvent was removed under reduced pressure, and the obtained residue was purified by thin-layer silica gel chromatography (dichloromethane/methanol/triethylamine=85/7/7) to obtain C-[1-(3,4-dichloro-benzyl)-piperidin-4-yl]-methylamine. The compound was identified by LC-MS.

Workup

  1. additionwere added at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by thin-layer silica gel chromatography (dichloromethane/methanol/triethylamine=85/7/7)

Sources & evidence

ORD record
ord-7113bd673bd1425fb34e2734d68d0963
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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